# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1a #TrackingRef '1.cif' _audit_creation_date 2012-08-14 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ; ? 2012-08-17 # Formatted by publCIF ; #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H26 Au N O' _chemical_formula_moiety 'C19 H26 Au N O' _chemical_formula_weight 481.39 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 7.7081(9) _cell_length_b 8.6036(9) _cell_length_c 15.1979(18) _cell_angle_alpha 86.966(6) _cell_angle_beta 80.202(6) _cell_angle_gamma 69.316(5) _cell_volume 929.14(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6590 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 293 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468.00 _exptl_absorpt_coefficient_mu 7.946 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 8961 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4229 _reflns_number_gt 2872 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1741 _refine_ls_number_restraints 195 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4229 _refine_ls_number_parameters 263 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0884P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.540 _refine_diff_density_min -1.160 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Au Au -2.0133 8.8022 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.25267(5) 0.96080(5) 0.98154(2) 0.0905(3) Uani 1.0 2 d . . . C2 C 0.4545(13) 0.3314(15) 0.8509(7) 0.092(3) Uani 1.0 2 d . . . C4 C 0.4836(12) 0.2046(13) 0.7076(8) 0.086(3) Uani 1.0 2 d . . . C5 C 0.4297(12) 0.3624(13) 0.6721(7) 0.086(3) Uani 1.0 2 d . . . C6 C 0.3784(12) 0.5018(13) 0.7253(7) 0.087(3) Uani 1.0 2 d . . . C7 C 0.3494(15) 0.6330(17) 0.8680(8) 0.093(3) Uani 1.0 2 d . . . C8 C 0.3127(15) 0.7517(18) 0.9129(10) 0.102(4) Uani 1.0 2 d . . . C9 C 0.206(5) 1.151(4) 1.0559(17) 0.084(4) Uani 0.540(11) 2 d . . . C10 C 0.153(4) 1.366(3) 1.1775(16) 0.105(4) Uani 0.540(11) 2 d . . . C11 C 0.096(4) 1.5465(17) 1.1441(12) 0.096(3) Uani 0.540(11) 2 d . . . C12 C 0.067(3) 1.6634(17) 1.2249(11) 0.097(4) Uani 0.540(11) 2 d . . . C13 C -0.016(3) 1.8537(16) 1.2031(12) 0.100(4) Uani 0.540(11) 2 d . . . C15 C 0.5827(16) -0.0905(14) 0.6800(9) 0.104(3) Uani 1.0 2 d . . . C16 C 0.6276(16) -0.2030(16) 0.6041(11) 0.119(4) Uani 1.0 2 d . . . C17 C 0.8046(15) -0.2096(14) 0.5349(9) 0.105(3) Uani 1.0 2 d . . . C18 C 0.9801(14) -0.2897(15) 0.5702(8) 0.103(3) Uani 1.0 2 d . . . C19 C 1.1525(16) -0.2951(16) 0.5018(9) 0.110(4) Uani 1.0 2 d . . . C1 C 0.3936(11) 0.4885(13) 0.8147(7) 0.079(3) Uani 1.0 2 d . . . H2 H 0.4671 0.3195 0.9109 0.1101 Uiso 1.0 2 calc R . . C3 C 0.4967(13) 0.1917(13) 0.7987(8) 0.089(3) Uani 1.0 2 d . . . H3 H 0.5346 0.0872 0.8247 0.1070 Uiso 1.0 2 calc R . . H5 H 0.4280 0.3750 0.6111 0.1033 Uiso 1.0 2 calc R . . H6 H 0.3327 0.6065 0.7003 0.1042 Uiso 1.0 2 calc R . . H15A H 0.4835 -0.1076 0.7235 0.1245 Uiso 1.0 2 calc R . . H15B H 0.6926 -0.1138 0.7085 0.1245 Uiso 1.0 2 calc R . . H16A H 0.5201 -0.1706 0.5731 0.1425 Uiso 1.0 2 calc R . . H16B H 0.6456 -0.3142 0.6268 0.1425 Uiso 1.0 2 calc R . . H17A H 0.8075 -0.2697 0.4822 0.1261 Uiso 1.0 2 calc R . . H17B H 0.7950 -0.0973 0.5171 0.1261 Uiso 1.0 2 calc R . . H18A H 0.9902 -0.4021 0.5879 0.1235 Uiso 1.0 2 calc R . . H18B H 0.9775 -0.2296 0.6230 0.1235 Uiso 1.0 2 calc R . . H19A H 1.2643 -0.3498 0.5273 0.1649 Uiso 1.0 2 calc R . . H19B H 1.1452 -0.1838 0.4856 0.1649 Uiso 1.0 2 calc R . . H19C H 1.1561 -0.3550 0.4496 0.1649 Uiso 1.0 2 calc R . . O1 O 0.5233(11) 0.0784(9) 0.6503(6) 0.102(2) Uani 1.0 2 d . . . N1 N 0.195(3) 1.259(3) 1.1034(14) 0.094(3) Uani 0.540(11) 2 d . . . H10A H 0.2616 1.3405 1.2071 0.1258 Uiso 0.540(11) 2 calc R . . H10B H 0.0504 1.3524 1.2200 0.1258 Uiso 0.540(11) 2 calc R . . H11A H -0.0188 1.5757 1.1192 0.1155 Uiso 0.540(11) 2 calc R . . H11B H 0.1943 1.5583 1.0979 0.1155 Uiso 0.540(11) 2 calc R . . H12A H 0.1863 1.6403 1.2448 0.1167 Uiso 0.540(11) 2 calc R . . H12B H -0.0177 1.6380 1.2737 0.1167 Uiso 0.540(11) 2 calc R . . H13A H 0.0575 1.8743 1.1483 0.1197 Uiso 0.540(11) 2 calc R . . H13B H -0.1432 1.8786 1.1915 0.1197 Uiso 0.540(11) 2 calc R . . C14 C -0.023(5) 1.976(3) 1.2750(16) 0.106(5) Uani 0.540(11) 2 d . . . H14A H -0.0758 2.0883 1.2547 0.1269 Uiso 0.540(11) 2 calc R . . H14B H 0.1026 1.9569 1.2857 0.1269 Uiso 0.540(11) 2 calc R . . H14C H -0.0984 1.9607 1.3293 0.1269 Uiso 0.540(11) 2 calc R . . C9A C 0.198(6) 1.180(5) 1.031(3) 0.088(4) Uani 0.460(11) 2 d . . . N1A N 0.182(3) 1.301(3) 1.0531(15) 0.092(3) Uani 0.460(11) 2 d . . . C10A C 0.094(4) 1.474(3) 1.0715(12) 0.102(4) Uani 0.460(11) 2 d . . . H10C H -0.0350 1.5119 1.0605 0.1225 Uiso 0.460(11) 2 calc R . . H10D H 0.1604 1.5361 1.0337 0.1225 Uiso 0.460(11) 2 calc R . . C11A C 0.099(5) 1.499(3) 1.1712(13) 0.100(4) Uani 0.460(11) 2 d . . . H11C H 0.2223 1.4390 1.1861 0.1202 Uiso 0.460(11) 2 calc R . . H11D H 0.0069 1.4624 1.2099 0.1202 Uiso 0.460(11) 2 calc R . . C13A C 0.027(4) 1.759(3) 1.2752(12) 0.100(4) Uani 0.460(11) 2 d . . . H13C H -0.0563 1.7141 1.3152 0.1202 Uiso 0.460(11) 2 calc R . . H13D H 0.1488 1.7156 1.2942 0.1202 Uiso 0.460(11) 2 calc R . . C12A C 0.048(4) 1.691(3) 1.1789(11) 0.099(3) Uani 0.460(11) 2 d . . . H12C H -0.0689 1.7457 1.1564 0.1192 Uiso 0.460(11) 2 calc R . . H12D H 0.1450 1.7213 1.1406 0.1192 Uiso 0.460(11) 2 calc R . . C14A C -0.050(5) 1.950(3) 1.2870(19) 0.097(4) Uani 0.460(11) 2 d . . . H14D H -0.0575 1.9777 1.3483 0.1162 Uiso 0.460(11) 2 calc R . . H14E H -0.1728 1.9951 1.2704 0.1162 Uiso 0.460(11) 2 calc R . . H14F H 0.0329 1.9965 1.2496 0.1162 Uiso 0.460(11) 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Au1 0.0889(3) 0.1018(4) 0.0778(3) -0.0311(3) -0.01360(19) 0.0111(2) C2 0.071(5) 0.123(8) 0.070(6) -0.026(6) -0.010(4) 0.024(6) C4 0.055(4) 0.096(6) 0.101(7) -0.025(5) -0.004(4) 0.011(6) C5 0.077(5) 0.105(7) 0.083(6) -0.039(5) -0.020(5) 0.018(5) C6 0.075(5) 0.097(6) 0.089(7) -0.037(5) -0.005(5) 0.018(5) C7 0.073(6) 0.112(8) 0.079(7) -0.019(6) -0.008(5) 0.009(6) C8 0.068(6) 0.115(9) 0.110(9) -0.022(6) -0.004(6) 0.014(8) C9 0.080(6) 0.091(8) 0.074(9) -0.028(6) -0.008(7) 0.013(6) C10 0.101(7) 0.114(7) 0.092(7) -0.027(6) -0.020(6) 0.011(6) C11 0.092(6) 0.108(6) 0.091(7) -0.038(6) -0.017(6) 0.007(5) C12 0.092(6) 0.113(6) 0.092(7) -0.042(6) -0.014(6) 0.002(6) C13 0.092(6) 0.116(6) 0.096(7) -0.042(6) -0.013(6) 0.003(6) C15 0.091(7) 0.101(7) 0.124(8) -0.048(6) -0.003(6) 0.009(6) C16 0.083(6) 0.102(7) 0.168(12) -0.034(6) -0.004(7) -0.017(7) C17 0.102(6) 0.095(6) 0.121(8) -0.036(6) -0.019(5) -0.008(6) C18 0.091(6) 0.109(7) 0.109(9) -0.039(6) -0.008(5) -0.005(6) C19 0.105(6) 0.108(8) 0.117(9) -0.044(6) -0.003(6) 0.006(7) C1 0.057(4) 0.100(6) 0.078(6) -0.030(5) 0.004(4) -0.009(5) C3 0.068(5) 0.090(6) 0.098(8) -0.018(5) -0.005(5) 0.010(6) O1 0.100(5) 0.092(5) 0.112(6) -0.035(4) -0.009(4) 0.005(4) N1 0.088(6) 0.098(7) 0.087(7) -0.025(6) -0.015(6) 0.012(5) C14 0.092(8) 0.120(8) 0.102(8) -0.040(8) -0.001(7) 0.000(7) C9A 0.080(6) 0.094(8) 0.082(9) -0.022(7) -0.011(8) 0.009(7) N1A 0.087(6) 0.099(7) 0.079(7) -0.022(6) -0.010(6) 0.014(6) C10A 0.102(7) 0.107(7) 0.087(7) -0.028(6) -0.008(7) 0.008(6) C11A 0.094(6) 0.115(6) 0.090(7) -0.035(6) -0.016(6) 0.004(6) C13A 0.096(6) 0.115(7) 0.095(7) -0.045(6) -0.012(6) 0.004(6) C12A 0.091(6) 0.116(6) 0.093(7) -0.040(6) -0.012(6) 0.005(5) C14A 0.090(7) 0.111(7) 0.100(8) -0.052(7) -0.009(7) 0.003(6) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Au1 C8 1.996(16) yes . . Au1 C9 1.93(3) yes . . Au1 C9A 1.94(5) yes . . C2 C1 1.382(15) yes . . C2 C3 1.384(17) yes . . C4 C5 1.381(15) yes . . C4 C3 1.402(17) yes . . C4 O1 1.343(14) yes . . C5 C6 1.381(16) yes . . C6 C1 1.379(15) yes . . C7 C8 1.18(2) yes . . C7 C1 1.425(18) yes . . C9 N1 1.18(4) yes . . C10 C11 1.54(3) yes . . C10 N1 1.42(3) yes . . C11 C12 1.56(3) yes . . C12 C13 1.573(19) yes . . C13 C14 1.54(3) yes . . C15 C16 1.46(2) yes . . C15 O1 1.433(14) yes . . C16 C17 1.560(18) yes . . C17 C18 1.464(16) yes . . C18 C19 1.529(17) yes . . C9A N1A 1.07(5) yes . . N1A C10A 1.42(4) yes . . C10A C11A 1.55(3) yes . . C11A C12A 1.56(3) yes . . C13A C12A 1.57(3) yes . . C13A C14A 1.55(3) yes . . C2 H2 0.930 no . . C5 H5 0.930 no . . C6 H6 0.930 no . . C10 H10A 0.970 no . . C10 H10B 0.970 no . . C11 H11A 0.970 no . . C11 H11B 0.970 no . . C12 H12A 0.970 no . . C12 H12B 0.970 no . . C13 H13A 0.970 no . . C13 H13B 0.970 no . . C15 H15A 0.970 no . . C15 H15B 0.970 no . . C16 H16A 0.970 no . . C16 H16B 0.970 no . . C17 H17A 0.970 no . . C17 H17B 0.970 no . . C18 H18A 0.970 no . . C18 H18B 0.970 no . . C19 H19A 0.960 no . . C19 H19B 0.960 no . . C19 H19C 0.960 no . . C3 H3 0.930 no . . C14 H14A 0.960 no . . C14 H14B 0.960 no . . C14 H14C 0.960 no . . C10A H10C 0.970 no . . C10A H10D 0.970 no . . C11A H11C 0.970 no . . C11A H11D 0.970 no . . C13A H13C 0.970 no . . C13A H13D 0.970 no . . C12A H12C 0.970 no . . C12A H12D 0.970 no . . C14A H14D 0.960 no . . C14A H14E 0.960 no . . C14A H14F 0.960 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C8 Au1 C9 174.9(9) yes . . . C8 Au1 C9A 171.5(11) yes . . . C1 C2 C3 120.7(10) yes . . . C5 C4 C3 117.0(11) yes . . . C5 C4 O1 116.4(10) yes . . . C3 C4 O1 126.6(10) yes . . . C4 C5 C6 121.5(10) yes . . . C5 C6 C1 121.2(10) yes . . . C8 C7 C1 179.3(14) yes . . . Au1 C8 C7 176.2(14) yes . . . Au1 C9 N1 173(3) yes . . . C11 C10 N1 108.7(18) yes . . . C10 C11 C12 108.4(15) yes . . . C11 C12 C13 113.9(14) yes . . . C12 C13 C14 116.7(16) yes . . . C16 C15 O1 109.9(11) yes . . . C15 C16 C17 115.8(13) yes . . . C16 C17 C18 112.7(11) yes . . . C17 C18 C19 112.2(11) yes . . . C2 C1 C6 118.2(10) yes . . . C2 C1 C7 121.0(10) yes . . . C6 C1 C7 120.8(10) yes . . . C2 C3 C4 121.3(10) yes . . . C4 O1 C15 120.9(10) yes . . . C9 N1 C10 164(3) yes . . . Au1 C9A N1A 173(4) yes . . . C9A N1A C10A 158(4) yes . . . N1A C10A C11A 106.7(17) yes . . . C10A C11A C12A 103.0(16) yes . . . C12A C13A C14A 116.6(17) yes . . . C11A C12A C13A 115.6(15) yes . . . C1 C2 H2 119.672 no . . . H2 C2 C3 119.677 no . . . C4 C5 H5 119.257 no . . . C6 C5 H5 119.267 no . . . C5 C6 H6 119.396 no . . . C1 C6 H6 119.410 no . . . C11 C10 H10A 109.950 no . . . C11 C10 H10B 109.943 no . . . N1 C10 H10A 109.941 no . . . N1 C10 H10B 109.940 no . . . H10A C10 H10B 108.332 no . . . C10 C11 H11A 110.017 no . . . C10 C11 H11B 110.009 no . . . C12 C11 H11A 110.007 no . . . C12 C11 H11B 110.001 no . . . H11A C11 H11B 108.380 no . . . C11 C12 H12A 108.774 no . . . C11 C12 H12B 108.772 no . . . C13 C12 H12A 108.772 no . . . C13 C12 H12B 108.773 no . . . H12A C12 H12B 107.662 no . . . C12 C13 H13A 108.108 no . . . C12 C13 H13B 108.109 no . . . H13A C13 H13B 107.310 no . . . H13A C13 C14 108.103 no . . . H13B C13 C14 108.106 no . . . C16 C15 H15A 109.686 no . . . C16 C15 H15B 109.685 no . . . H15A C15 H15B 108.178 no . . . H15A C15 O1 109.684 no . . . H15B C15 O1 109.681 no . . . C15 C16 H16A 108.321 no . . . C15 C16 H16B 108.328 no . . . C17 C16 H16A 108.331 no . . . C17 C16 H16B 108.323 no . . . H16A C16 H16B 107.415 no . . . C16 C17 H17A 109.053 no . . . C16 C17 H17B 109.044 no . . . C18 C17 H17A 109.053 no . . . C18 C17 H17B 109.048 no . . . H17A C17 H17B 107.810 no . . . C17 C18 H18A 109.171 no . . . C17 C18 H18B 109.174 no . . . C19 C18 H18A 109.165 no . . . C19 C18 H18B 109.175 no . . . H18A C18 H18B 107.889 no . . . C18 C19 H19A 109.466 no . . . C18 C19 H19B 109.469 no . . . C18 C19 H19C 109.474 no . . . H19A C19 H19B 109.471 no . . . H19A C19 H19C 109.477 no . . . H19B C19 H19C 109.470 no . . . C2 C3 H3 119.341 no . . . C4 C3 H3 119.344 no . . . C13 C14 H14A 109.471 no . . . C13 C14 H14B 109.476 no . . . C13 C14 H14C 109.477 no . . . H14A C14 H14B 109.468 no . . . H14A C14 H14C 109.470 no . . . H14B C14 H14C 109.466 no . . . N1A C10A H10C 110.385 no . . . N1A C10A H10D 110.380 no . . . H10C C10A H10D 108.599 no . . . H10C C10A C11A 110.379 no . . . H10D C10A C11A 110.380 no . . . C10A C11A H11C 111.170 no . . . C10A C11A H11D 111.167 no . . . H11C C11A H11D 109.106 no . . . H11C C11A C12A 111.173 no . . . H11D C11A C12A 111.171 no . . . H13C C13A H13D 107.326 no . . . H13C C13A C12A 108.147 no . . . H13C C13A C14A 108.145 no . . . H13D C13A C12A 108.141 no . . . H13D C13A C14A 108.150 no . . . C11A C12A H12C 108.392 no . . . C11A C12A H12D 108.389 no . . . C13A C12A H12C 108.389 no . . . C13A C12A H12D 108.394 no . . . H12C C12A H12D 107.448 no . . . C13A C14A H14D 109.470 no . . . C13A C14A H14E 109.480 no . . . C13A C14A H14F 109.473 no . . . H14D C14A H14E 109.467 no . . . H14D C14A H14F 109.467 no . . . H14E C14A H14F 109.471 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 C2 C3 C4 1.5(15) no . . . . C3 C2 C1 C6 -0.7(14) no . . . . C3 C2 C1 C7 179.9(8) no . . . . C5 C4 C3 C2 1.0(14) no . . . . C3 C4 C5 C6 -4.4(14) no . . . . C5 C4 O1 C15 179.3(8) no . . . . O1 C4 C5 C6 177.4(8) no . . . . C3 C4 O1 C15 1.3(14) no . . . . O1 C4 C3 C2 179.0(9) no . . . . C4 C5 C6 C1 5.4(15) no . . . . C5 C6 C1 C2 -2.7(14) no . . . . C5 C6 C1 C7 176.8(8) no . . . . N1 C10 C11 C12 -175.1(17) no . . . . C10 C11 C12 C13 -172.8(17) no . . . . C11 C12 C13 C14 -171.4(17) no . . . . C16 C15 O1 C4 -176.5(9) no . . . . O1 C15 C16 C17 68.1(13) no . . . . C15 C16 C17 C18 69.9(13) no . . . . C16 C17 C18 C19 -179.9(10) no . . . . C9A N1A C10A C11A 125(8) no . . . . N1A C10A C11A C12A 166(2) no . . . . C10A C11A C12A C13A 176(2) no . . . . C14A C13A C12A C11A -172(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 C2 C5 2.748(15) no . . C2 C8 3.52(2) no . . C4 C1 2.818(16) no . . C6 C8 3.52(2) no . . C6 C3 2.740(15) no . . C6 O1 3.598(14) no . . C9 C11 3.49(4) no . . C15 C18 3.156(14) no . . C15 C3 2.917(18) no . . C17 O1 3.047(13) no . . C9A C11A 3.35(5) no . . Au1 Au1 3.6582(7) no . 2_577 Au1 C13 3.599(19) no . 2_587 C2 C12 3.69(3) no . 2_677 C2 C9A 3.57(4) no . 1_545 C2 N1A 3.47(3) no . 1_545 C5 C19 3.693(15) no . 2_756 C10 C15 3.47(3) no . 2_667 C12 C2 3.69(3) no . 2_677 C13 Au1 3.599(19) no . 2_587 C15 C10 3.47(3) no . 2_667 C19 C5 3.693(15) no . 2_756 C19 C13A 3.70(3) no . 1_634 C9A C2 3.57(4) no . 1_565 C9A C10A 3.51(5) no . 2_587 N1A C2 3.47(3) no . 1_565 N1A C10A 3.15(3) no . 2_587 C10A C9A 3.51(5) no . 2_587 C10A N1A 3.15(3) no . 2_587 C10A C10A 2.74(4) no . 2_587 C13A C19 3.70(3) no . 1_476 C2 H6 3.2106 no . . C4 H2 3.2626 no . . C4 H6 3.2381 no . . C4 H15A 2.6837 no . . C4 H15B 2.6428 no . . C5 H3 3.2150 no . . C6 H2 3.2119 no . . C7 H2 2.6098 no . . C7 H6 2.5995 no . . C8 H2 3.4815 no . . C8 H6 3.4855 no . . C9 H10A 3.0575 no . . C9 H10B 2.9406 no . . C9 H11A 3.5540 no . . C9 H11B 3.5644 no . . C10 H12A 2.7270 no . . C10 H12B 2.6196 no . . C11 H13A 2.7321 no . . C11 H13B 2.8513 no . . C12 H10A 2.6533 no . . C12 H10B 2.7271 no . . C12 H14A 3.4562 no . . C12 H14B 2.8527 no . . C12 H14C 2.8501 no . . C13 H11A 2.7768 no . . C13 H11B 2.8775 no . . C15 H3 2.6433 no . . C15 H17A 3.3542 no . . C15 H17B 2.7163 no . . C15 H18A 3.4589 no . . C15 H18B 2.8430 no . . C16 H18A 2.6899 no . . C16 H18B 2.6890 no . . C17 H15A 3.3804 no . . C17 H15B 2.7081 no . . C17 H19A 3.2985 no . . C17 H19B 2.6887 no . . C17 H19C 2.6776 no . . C18 H15B 2.8281 no . . C18 H16A 3.3183 no . . C18 H16B 2.6542 no . . C19 H17A 2.6571 no . . C19 H17B 2.6564 no . . C1 H3 3.2365 no . . C1 H5 3.2336 no . . H2 H3 2.3005 no . . C3 H5 3.2168 no . . C3 H15A 2.9127 no . . C3 H15B 2.8183 no . . H3 H15A 2.5045 no . . H3 H15B 2.3867 no . . H3 O1 2.6718 no . . H5 H6 2.2930 no . . H5 O1 2.4641 no . . H15A H16A 2.3240 no . . H15A H16B 2.2285 no . . H15B H16A 2.7813 no . . H15B H16B 2.3386 no . . H15B H17B 2.8908 no . . H15B H18A 3.1308 no . . H15B H18B 2.2634 no . . H16A H17A 2.3010 no . . H16A H17B 2.4257 no . . H16A H18A 3.5043 no . . H16A H18B 3.5868 no . . H16A O1 2.5057 no . . H16B H17A 2.4185 no . . H16B H17B 2.8501 no . . H16B H18A 2.4640 no . . H16B H18B 2.8880 no . . H16B O1 3.1922 no . . H17A H18A 2.3036 no . . H17A H18B 2.7868 no . . H17A H19A 3.5212 no . . H17A H19B 2.9554 no . . H17A H19C 2.4890 no . . H17B H18A 2.7868 no . . H17B H18B 2.3042 no . . H17B H19A 3.5262 no . . H17B H19B 2.5003 no . . H17B H19C 2.9372 no . . H17B O1 2.7229 no . . H18A H19A 2.3411 no . . H18A H19B 2.8313 no . . H18A H19C 2.3618 no . . H18B H19A 2.3496 no . . H18B H19B 2.3533 no . . H18B H19C 2.8313 no . . H18B O1 3.5383 no . . N1 H11A 2.6408 no . . N1 H11B 2.5718 no . . H10A H11A 2.8554 no . . H10A H11B 2.4107 no . . H10A H12A 2.5107 no . . H10A H12B 2.8021 no . . H10B H11A 2.3589 no . . H10B H11B 2.8554 no . . H10B H12A 3.0719 no . . H10B H12B 2.4763 no . . H11A H12A 2.8648 no . . H11A H12B 2.4381 no . . H11A H13A 2.9012 no . . H11A H13B 2.6640 no . . H11B H12A 2.3606 no . . H11B H12B 2.8632 no . . H11B H13A 2.6474 no . . H11B H13B 3.2364 no . . H12A H13A 2.4406 no . . H12A H13B 2.8552 no . . H12A C14 2.7869 no . . H12A H14B 2.6501 no . . H12A H14C 3.0340 no . . H12B H13A 2.8543 no . . H12B H13B 2.3460 no . . H12B C14 2.9001 no . . H12B H14B 3.2136 no . . H12B H14C 2.7669 no . . H13A H14A 2.3392 no . . H13A H14B 2.3594 no . . H13A H14C 2.8322 no . . H13B H14A 2.3372 no . . H13B H14B 2.8322 no . . H13B H14C 2.3616 no . . C9A H10C 2.7978 no . . C9A H10D 2.9769 no . . C9A H11C 3.3976 no . . C9A H11D 3.5017 no . . N1A H11C 2.5140 no . . N1A H11D 2.7140 no . . C10A H12C 2.5300 no . . C10A H12D 2.5997 no . . H10C H11C 2.8739 no . . H10C H11D 2.3442 no . . H10C C12A 2.7203 no . . H10C H12C 2.4593 no . . H10C H12D 3.0371 no . . H10D H11C 2.4863 no . . H10D H11D 2.8719 no . . H10D C12A 2.4969 no . . H10D H12C 2.6137 no . . H10D H12D 2.2938 no . . C11A H13C 2.7599 no . . C11A H13D 2.8710 no . . H11C C13A 2.9049 no . . H11C H13C 3.0863 no . . H11C H13D 2.7970 no . . H11C H12C 2.8705 no . . H11C H12D 2.3813 no . . H11D C13A 2.8461 no . . H11D H13C 2.6157 no . . H11D H13D 3.1683 no . . H11D H12C 2.4272 no . . H11D H12D 2.8726 no . . H13C H12C 2.4287 no . . H13C H12D 2.8462 no . . H13C H14D 2.3458 no . . H13C H14E 2.3691 no . . H13C H14F 2.8388 no . . H13D H12C 2.8463 no . . H13D H12D 2.3377 no . . H13D H14D 2.3473 no . . H13D H14E 2.8388 no . . H13D H14F 2.3676 no . . C12A H14D 3.4534 no . . C12A H14E 2.8496 no . . C12A H14F 2.8513 no . . H12C C14A 2.7770 no . . H12C H14E 2.6378 no . . H12C H14F 3.0303 no . . H12D C14A 2.8859 no . . H12D H14E 3.1963 no . . H12D H14F 2.7544 no . . Au1 H2 3.2030 no . 2_667 Au1 H3 3.3499 no . 1_565 Au1 H3 3.5455 no . 2_667 Au1 H13A 2.9217 no . 1_545 Au1 H13A 3.2460 no . 2_587 Au1 H13B 3.0142 no . 2_587 Au1 H12C 3.2711 no . 2_587 Au1 H12D 3.2825 no . 1_545 C2 H11A 3.1219 no . 2_577 C2 H11B 3.3833 no . 2_677 C2 H12A 2.9849 no . 2_677 C2 H13A 3.5491 no . 2_677 C2 H13B 3.6258 no . 2_577 C2 H10C 3.1170 no . 2_577 C2 H10D 3.3935 no . 1_545 C2 H11C 3.6474 no . 2_677 C2 H11D 3.6242 no . 2_577 C2 H13D 3.3621 no . 2_677 C2 H12C 3.2856 no . 2_577 C2 H12D 2.9828 no . 2_677 C4 H19B 3.6973 no . 2_756 C4 H12A 3.4513 no . 2_677 C4 H12B 3.3269 no . 2_577 C4 H13B 3.0966 no . 2_577 C4 H14B 3.0133 no . 2_677 C4 H13C 3.1926 no . 2_577 C4 H13D 3.1384 no . 2_677 C4 H12C 3.3993 no . 2_577 C4 H14E 3.3727 no . 2_577 C4 H14F 3.6681 no . 2_677 C5 H16B 3.6965 no . 1_565 C5 H17A 3.4877 no . 2_656 C5 H18A 3.6840 no . 1_465 C5 H19A 3.2793 no . 1_465 C5 H19A 3.4900 no . 2_756 C5 H19B 3.6057 no . 2_756 C5 H19C 3.3880 no . 2_756 C5 H12A 3.4029 no . 2_677 C5 H12B 3.1431 no . 2_577 C5 H11D 3.3853 no . 2_577 C5 H13C 3.1451 no . 2_577 C5 H13D 3.2029 no . 2_677 C6 H16B 3.1611 no . 1_565 C6 H18B 3.6768 no . 1_465 C6 H19A 3.3405 no . 1_465 C6 H10B 3.0720 no . 2_577 C6 H11A 3.5529 no . 2_577 C6 H12A 3.2444 no . 2_677 C6 H12B 3.3940 no . 2_577 C6 H14A 3.4691 no . 2_587 C6 H11D 2.8762 no . 2_577 C6 H13D 3.4270 no . 2_677 C7 H15A 3.3481 no . 1_565 C7 H10A 3.1038 no . 2_677 C7 H10B 3.5239 no . 2_577 C7 H11A 3.5755 no . 2_577 C7 H11B 3.5962 no . 1_545 C7 H11B 3.4339 no . 2_677 C7 H12A 3.6973 no . 2_677 C7 H14A 3.3116 no . 2_587 C7 H10C 3.1149 no . 2_577 C7 H10D 2.9239 no . 1_545 C7 H11C 3.1050 no . 2_677 C7 H11D 3.5242 no . 2_577 C8 H2 3.3266 no . 2_667 C8 H15A 3.3096 no . 1_565 C8 H10A 3.3166 no . 2_677 C8 H11B 3.3478 no . 1_545 C8 H13A 3.6689 no . 2_587 C8 H13B 3.4027 no . 2_587 C8 H14A 3.3397 no . 2_587 C8 H10C 3.5952 no . 2_577 C8 H10D 2.9383 no . 1_545 C8 H11C 3.4750 no . 2_677 C8 H12D 3.5113 no . 1_545 C8 H14E 3.5204 no . 2_587 C9 H2 3.3494 no . 1_565 C9 H3 3.0698 no . 2_667 C9 H11A 3.5997 no . 2_587 C9 H13A 3.1578 no . 1_545 C9 H14A 3.5448 no . 1_545 C10 H15A 3.4288 no . 2_667 C10 H15B 2.7613 no . 2_667 C10 H16B 3.5225 no . 2_667 C10 H18A 3.5443 no . 2_667 C10 H18B 3.3192 no . 2_667 C10 H14A 3.4914 no . 1_545 C12 H18A 3.5967 no . 2_667 C12 H19C 3.5830 no . 1_476 C13 H15A 3.5101 no . 2_577 C15 H10A 2.7388 no . 2_667 C15 H10B 3.4613 no . 2_667 C15 H13B 3.5183 no . 2_577 C15 H14B 3.1529 no . 2_677 C15 H14C 3.5241 no . 2_577 C15 H11C 3.5499 no . 2_667 C15 H14E 2.9410 no . 2_577 C15 H14F 3.6655 no . 2_677 C16 H6 3.3521 no . 1_545 C16 H19C 3.6456 no . 2_746 C16 H10A 3.1829 no . 2_667 C16 H14E 3.5755 no . 2_577 C17 H5 3.6951 no . 2_656 C17 H18A 3.6155 no . 2_746 C17 H19B 3.5320 no . 2_756 C17 H19C 3.6483 no . 2_746 C17 H14C 3.4589 no . 1_634 C17 H13C 3.3546 no . 1_634 C17 H14D 3.3873 no . 1_634 C18 H6 3.4668 no . 1_645 C18 H17A 3.6298 no . 2_746 C18 H18A 3.5947 no . 2_746 C18 H19C 3.6075 no . 2_746 C18 H10A 3.6599 no . 2_667 C18 H10B 3.1875 no . 2_667 C18 H12B 3.6823 no . 2_667 C18 H14A 3.5615 no . 2_677 C18 H14B 3.5064 no . 2_677 C18 H11D 3.5867 no . 2_667 C18 H14D 3.2900 no . 2_677 C19 H5 3.4304 no . 1_645 C19 H5 3.2467 no . 2_756 C19 H6 3.4745 no . 1_645 C19 H16A 3.6964 no . 1_655 C19 H16B 3.6748 no . 2_746 C19 H17A 3.6451 no . 2_746 C19 H17B 3.5305 no . 2_756 C19 H18A 3.5734 no . 2_746 C19 H14C 3.6832 no . 1_634 C19 H13C 3.4760 no . 1_634 C19 H13D 3.1567 no . 1_634 C19 H14D 3.4052 no . 1_634 C19 H14D 3.4437 no . 2_677 C1 H10A 3.4273 no . 2_677 C1 H10B 3.3311 no . 2_577 C1 H11A 3.1215 no . 2_577 C1 H11B 3.5347 no . 2_677 C1 H12A 3.0176 no . 2_677 C1 H10C 3.0759 no . 2_577 C1 H10D 3.4741 no . 1_545 C1 H11C 3.2313 no . 2_677 C1 H11D 3.0500 no . 2_577 C1 H13D 3.4940 no . 2_677 C1 H12C 3.6894 no . 2_577 C1 H12D 3.5395 no . 2_677 H2 Au1 3.2030 no . 2_667 H2 C8 3.3266 no . 2_667 H2 C9 3.3494 no . 1_545 H2 N1 3.4267 no . 1_545 H2 H11A 3.3551 no . 2_577 H2 H11B 3.5004 no . 1_545 H2 H11B 3.1211 no . 2_677 H2 H12A 3.3570 no . 2_677 H2 H13A 3.4264 no . 2_677 H2 C9A 3.0528 no . 1_545 H2 N1A 2.8476 no . 1_545 H2 C10A 3.3548 no . 1_545 H2 H10C 3.0897 no . 2_577 H2 H10D 2.8813 no . 1_545 H2 H12C 3.6225 no . 2_577 H2 H12D 2.8580 no . 2_677 C3 H11A 3.5533 no . 2_577 C3 H12A 3.2156 no . 2_677 C3 H13A 3.5062 no . 2_677 C3 H13B 2.9715 no . 2_577 C3 H14B 2.9761 no . 2_677 C3 H13D 3.1942 no . 2_677 C3 H12C 3.1062 no . 2_577 C3 H12D 3.3825 no . 2_677 C3 H14F 3.3732 no . 2_677 H3 Au1 3.3499 no . 1_545 H3 Au1 3.5455 no . 2_667 H3 C9 3.0698 no . 2_667 H3 N1 3.2311 no . 2_667 H3 H10A 3.4770 no . 2_667 H3 H13A 3.3697 no . 2_677 H3 H13B 2.9776 no . 2_577 H3 C14 3.6654 no . 2_677 H3 H14B 2.9159 no . 2_677 H3 C9A 3.6400 no . 1_545 H3 C9A 3.4596 no . 2_667 H3 H13D 3.6327 no . 2_677 H3 H12C 3.3289 no . 2_577 H3 H12D 3.5364 no . 2_677 H3 H14E 3.6391 no . 2_577 H3 H14F 3.1647 no . 2_677 H5 C17 3.6951 no . 2_656 H5 C19 3.4304 no . 1_465 H5 C19 3.2467 no . 2_756 H5 H16A 3.2761 no . 2_656 H5 H16B 3.6594 no . 1_565 H5 H17A 2.8804 no . 2_656 H5 H18A 3.3088 no . 1_465 H5 H19A 2.6342 no . 1_465 H5 H19A 2.8431 no . 2_756 H5 H19B 3.2366 no . 2_756 H5 H19C 3.6765 no . 1_465 H5 H19C 3.1273 no . 2_756 H5 H12B 3.3795 no . 2_577 H5 H13C 3.2282 no . 2_577 H5 H13D 3.6066 no . 2_677 H6 C16 3.3521 no . 1_565 H6 C18 3.4668 no . 1_465 H6 C19 3.4745 no . 1_465 H6 H15A 3.1270 no . 1_565 H6 H16A 3.1805 no . 1_565 H6 H16B 2.7739 no . 1_565 H6 H18A 3.4027 no . 1_465 H6 H18B 3.0100 no . 1_465 H6 H19A 2.7498 no . 1_465 H6 H10B 2.8990 no . 2_577 H6 H12B 3.6971 no . 2_577 H6 C14 3.5367 no . 2_587 H6 H14A 2.7096 no . 2_587 H6 H14C 3.5610 no . 2_587 H6 H11D 2.9762 no . 2_577 H6 C14A 3.6598 no . 2_587 H6 H14D 3.5684 no . 2_587 H6 H14E 3.2339 no . 2_587 H6 H14F 3.5963 no . 2_587 H15A C7 3.3481 no . 1_545 H15A C8 3.3096 no . 1_545 H15A C10 3.4288 no . 2_667 H15A C13 3.5101 no . 2_577 H15A H6 3.1270 no . 1_545 H15A H10A 2.5868 no . 2_667 H15A H10B 3.6867 no . 2_667 H15A H13B 2.8101 no . 2_577 H15A C14 3.3226 no . 2_577 H15A H14A 3.0489 no . 2_577 H15A H14C 3.0172 no . 2_577 H15A H11C 3.3522 no . 2_667 H15A C14A 3.1604 no . 2_577 H15A H14D 3.4234 no . 2_577 H15A H14E 2.2311 no . 2_577 H15B C10 2.7613 no . 2_667 H15B N1 3.1904 no . 2_667 H15B H10A 2.2317 no . 2_667 H15B H10B 2.6346 no . 2_667 H15B C14 3.2092 no . 2_677 H15B H14A 3.1809 no . 2_677 H15B H14B 2.4265 no . 2_677 H15B C11A 3.6748 no . 2_667 H15B H11C 3.0680 no . 2_667 H15B H11D 3.4019 no . 2_667 H15B C14A 3.5190 no . 2_677 H15B H14D 3.3788 no . 2_677 H15B H14F 2.8164 no . 2_677 H16A C19 3.6964 no . 1_455 H16A H5 3.2761 no . 2_656 H16A H6 3.1805 no . 1_545 H16A H16A 3.5428 no . 2_656 H16A H17B 3.1517 no . 2_656 H16A H19A 3.0787 no . 1_455 H16A H19B 3.4188 no . 1_455 H16A O1 3.4908 no . 2_656 H16A H14C 3.2439 no . 2_577 H16A H14D 3.3877 no . 2_577 H16A H14E 3.2342 no . 2_577 H16B C5 3.6965 no . 1_545 H16B C6 3.1611 no . 1_545 H16B C10 3.5225 no . 2_667 H16B C19 3.6748 no . 2_746 H16B H5 3.6594 no . 1_545 H16B H6 2.7739 no . 1_545 H16B H19A 3.6351 no . 1_455 H16B H19A 3.6146 no . 2_746 H16B H19C 2.9078 no . 2_746 H16B H10A 2.7170 no . 2_667 H16B H10B 3.5000 no . 2_667 H16B H12A 3.3282 no . 2_667 H16B H12B 3.6960 no . 2_667 H16B H11C 3.1883 no . 2_667 H16B H13D 3.4961 no . 2_667 H17A C5 3.4877 no . 2_656 H17A C18 3.6298 no . 2_746 H17A C19 3.6451 no . 2_746 H17A H5 2.8804 no . 2_656 H17A H18A 2.8600 no . 2_746 H17A H19A 3.5216 no . 2_746 H17A H19C 3.2683 no . 2_746 H17A O1 3.4202 no . 2_656 H17A H12B 3.2462 no . 1_634 H17A H14C 3.1315 no . 1_634 H17A C13A 3.3479 no . 1_634 H17A H13C 2.5674 no . 1_634 H17A H13D 3.5132 no . 1_634 H17A C14A 3.6539 no . 1_634 H17A H14D 3.1846 no . 1_634 H17B C19 3.5305 no . 2_756 H17B H16A 3.1517 no . 2_656 H17B H19B 2.6142 no . 2_756 H17B H14B 3.5951 no . 2_677 H17B H14C 2.9000 no . 1_634 H17B H13C 3.3738 no . 1_634 H17B C14A 3.5489 no . 1_634 H17B H14D 2.7645 no . 1_634 H17B H14D 3.5273 no . 2_677 H18A C5 3.6840 no . 1_645 H18A C10 3.5443 no . 2_667 H18A C12 3.5967 no . 2_667 H18A C17 3.6155 no . 2_746 H18A C18 3.5947 no . 2_746 H18A C19 3.5734 no . 2_746 H18A H5 3.3088 no . 1_645 H18A H6 3.4027 no . 1_645 H18A H17A 2.8600 no . 2_746 H18A H18A 3.1878 no . 2_746 H18A H19C 2.8240 no . 2_746 H18A H10A 3.3388 no . 2_667 H18A H10B 2.9198 no . 2_667 H18A H12A 3.5720 no . 2_667 H18A H12B 2.8251 no . 2_667 H18A H11C 3.5938 no . 2_667 H18A H11D 3.0909 no . 2_667 H18A C13A 3.6428 no . 2_667 H18A H13C 2.9165 no . 2_667 H18A H13D 3.5369 no . 2_667 H18B C6 3.6768 no . 1_645 H18B C10 3.3192 no . 2_667 H18B H6 3.0100 no . 1_645 H18B H10A 3.2162 no . 2_667 H18B H10B 2.5645 no . 2_667 H18B C14 2.8887 no . 2_677 H18B H14A 2.6229 no . 2_677 H18B H14B 2.6156 no . 2_677 H18B H14C 2.9463 no . 2_677 H18B H11D 3.1418 no . 2_667 H18B C14A 3.0849 no . 2_677 H18B H14D 2.5301 no . 2_677 H18B H14E 3.5048 no . 2_677 H18B H14F 2.8320 no . 2_677 H19A C5 3.2793 no . 1_645 H19A C5 3.4900 no . 2_756 H19A C6 3.3405 no . 1_645 H19A H5 2.6342 no . 1_645 H19A H5 2.8431 no . 2_756 H19A H6 2.7498 no . 1_645 H19A H16A 3.0787 no . 1_655 H19A H16B 3.6351 no . 1_655 H19A H16B 3.6146 no . 2_746 H19A H17A 3.5216 no . 2_746 H19A H19A 3.6250 no . 2_846 H19A H14D 3.5174 no . 2_677 H19B C4 3.6973 no . 2_756 H19B C5 3.6057 no . 2_756 H19B C17 3.5320 no . 2_756 H19B H5 3.2366 no . 2_756 H19B H16A 3.4188 no . 1_655 H19B H17B 2.6142 no . 2_756 H19B H19B 3.1655 no . 2_756 H19B O1 3.3559 no . 2_756 H19B C14 3.6745 no . 1_634 H19B H14B 3.2354 no . 1_634 H19B H14C 3.2052 no . 1_634 H19B H14C 3.3866 no . 2_677 H19B C13A 3.5757 no . 1_634 H19B H13C 3.5309 no . 1_634 H19B H13D 3.0717 no . 1_634 H19B C14A 3.5574 no . 1_634 H19B H14D 2.8281 no . 1_634 H19B H14D 3.0034 no . 2_677 H19C C5 3.3880 no . 2_756 H19C C12 3.5830 no . 1_634 H19C C16 3.6456 no . 2_746 H19C C17 3.6483 no . 2_746 H19C C18 3.6075 no . 2_746 H19C H5 3.6765 no . 1_645 H19C H5 3.1273 no . 2_756 H19C H16B 2.9078 no . 2_746 H19C H17A 3.2683 no . 2_746 H19C H18A 2.8240 no . 2_746 H19C H12A 3.0839 no . 1_634 H19C H12B 3.1998 no . 1_634 H19C H14B 3.5260 no . 1_634 H19C H14C 3.3913 no . 1_634 H19C C13A 2.9857 no . 1_634 H19C H13C 2.7444 no . 1_634 H19C H13D 2.4129 no . 1_634 H19C C14A 3.6373 no . 1_634 H19C H14D 3.2165 no . 1_634 O1 H16A 3.4908 no . 2_656 O1 H17A 3.4202 no . 2_656 O1 H19B 3.3559 no . 2_756 O1 H13B 3.3807 no . 2_577 O1 H14B 3.1078 no . 2_677 O1 H14C 3.3693 no . 2_577 O1 H13C 3.3672 no . 2_577 O1 H14E 3.0276 no . 2_577 N1 H2 3.4267 no . 1_565 N1 H3 3.2311 no . 2_667 N1 H15B 3.1904 no . 2_667 N1 H14A 3.4615 no . 1_545 H10A C7 3.1038 no . 2_677 H10A C8 3.3166 no . 2_677 H10A C15 2.7388 no . 2_667 H10A C16 3.1829 no . 2_667 H10A C18 3.6599 no . 2_667 H10A C1 3.4273 no . 2_677 H10A H3 3.4770 no . 2_667 H10A H15A 2.5868 no . 2_667 H10A H15B 2.2317 no . 2_667 H10A H16B 2.7170 no . 2_667 H10A H18A 3.3388 no . 2_667 H10A H18B 3.2162 no . 2_667 H10B C6 3.0720 no . 2_577 H10B C7 3.5239 no . 2_577 H10B C15 3.4613 no . 2_667 H10B C18 3.1875 no . 2_667 H10B C1 3.3311 no . 2_577 H10B H6 2.8990 no . 2_577 H10B H15A 3.6867 no . 2_667 H10B H15B 2.6346 no . 2_667 H10B H16B 3.5000 no . 2_667 H10B H18A 2.9198 no . 2_667 H10B H18B 2.5645 no . 2_667 H10B C14 3.5096 no . 1_545 H10B H14A 2.7660 no . 1_545 H10B H14B 3.3988 no . 1_545 H11A C2 3.1219 no . 2_577 H11A C6 3.5529 no . 2_577 H11A C7 3.5755 no . 2_577 H11A C9 3.5997 no . 2_587 H11A C1 3.1215 no . 2_577 H11A H2 3.3551 no . 2_577 H11A C3 3.5533 no . 2_577 H11B C2 3.3833 no . 2_677 H11B C7 3.5962 no . 1_565 H11B C7 3.4339 no . 2_677 H11B C8 3.3478 no . 1_565 H11B C1 3.5347 no . 2_677 H11B H2 3.5004 no . 1_565 H11B H2 3.1211 no . 2_677 H12A C2 2.9849 no . 2_677 H12A C4 3.4513 no . 2_677 H12A C5 3.4029 no . 2_677 H12A C6 3.2444 no . 2_677 H12A C7 3.6973 no . 2_677 H12A C1 3.0176 no . 2_677 H12A H2 3.3570 no . 2_677 H12A C3 3.2156 no . 2_677 H12A H16B 3.3282 no . 2_667 H12A H18A 3.5720 no . 2_667 H12A H19C 3.0839 no . 1_476 H12B C4 3.3269 no . 2_577 H12B C5 3.1431 no . 2_577 H12B C6 3.3940 no . 2_577 H12B C18 3.6823 no . 2_667 H12B H5 3.3795 no . 2_577 H12B H6 3.6971 no . 2_577 H12B H16B 3.6960 no . 2_667 H12B H17A 3.2462 no . 1_476 H12B H18A 2.8251 no . 2_667 H12B H19C 3.1998 no . 1_476 H13A Au1 2.9217 no . 1_565 H13A Au1 3.2460 no . 2_587 H13A C2 3.5491 no . 2_677 H13A C8 3.6689 no . 2_587 H13A C9 3.1578 no . 1_565 H13A H2 3.4264 no . 2_677 H13A C3 3.5062 no . 2_677 H13A H3 3.3697 no . 2_677 H13B Au1 3.0142 no . 2_587 H13B C2 3.6258 no . 2_577 H13B C4 3.0966 no . 2_577 H13B C8 3.4027 no . 2_587 H13B C15 3.5183 no . 2_577 H13B C3 2.9715 no . 2_577 H13B H3 2.9776 no . 2_577 H13B H15A 2.8101 no . 2_577 H13B O1 3.3807 no . 2_577 C14 H3 3.6654 no . 2_677 C14 H6 3.5367 no . 2_587 C14 H15A 3.3226 no . 2_577 C14 H15B 3.2092 no . 2_677 C14 H18B 2.8887 no . 2_677 C14 H19B 3.6745 no . 1_476 C14 H10B 3.5096 no . 1_565 H14A C6 3.4691 no . 2_587 H14A C7 3.3116 no . 2_587 H14A C8 3.3397 no . 2_587 H14A C9 3.5448 no . 1_565 H14A C10 3.4914 no . 1_565 H14A C18 3.5615 no . 2_677 H14A H6 2.7096 no . 2_587 H14A H15A 3.0489 no . 2_577 H14A H15B 3.1809 no . 2_677 H14A H18B 2.6229 no . 2_677 H14A N1 3.4615 no . 1_565 H14A H10B 2.7660 no . 1_565 H14B C4 3.0133 no . 2_677 H14B C15 3.1529 no . 2_677 H14B C18 3.5064 no . 2_677 H14B C3 2.9761 no . 2_677 H14B H3 2.9159 no . 2_677 H14B H15B 2.4265 no . 2_677 H14B H17B 3.5951 no . 2_677 H14B H18B 2.6156 no . 2_677 H14B H19B 3.2354 no . 1_476 H14B H19C 3.5260 no . 1_476 H14B O1 3.1078 no . 2_677 H14B H10B 3.3988 no . 1_565 H14C C15 3.5241 no . 2_577 H14C C17 3.4589 no . 1_476 H14C C19 3.6832 no . 1_476 H14C H6 3.5610 no . 2_587 H14C H15A 3.0172 no . 2_577 H14C H16A 3.2439 no . 2_577 H14C H17A 3.1315 no . 1_476 H14C H17B 2.9000 no . 1_476 H14C H18B 2.9463 no . 2_677 H14C H19B 3.2052 no . 1_476 H14C H19B 3.3866 no . 2_677 H14C H19C 3.3913 no . 1_476 H14C O1 3.3693 no . 2_577 C9A H2 3.0528 no . 1_565 C9A H3 3.6400 no . 1_565 C9A H3 3.4596 no . 2_667 C9A H10C 2.9008 no . 2_587 C9A H10D 3.2395 no . 2_587 C9A H12C 3.1405 no . 2_587 N1A H2 2.8476 no . 1_565 N1A H10C 2.4371 no . 2_587 N1A H10D 3.0089 no . 2_587 N1A H12C 3.5195 no . 2_587 C10A H2 3.3548 no . 1_565 C10A H10C 2.1176 no . 2_587 C10A H10D 2.7565 no . 2_587 H10C C2 3.1170 no . 2_577 H10C C7 3.1149 no . 2_577 H10C C8 3.5952 no . 2_577 H10C C1 3.0759 no . 2_577 H10C H2 3.0897 no . 2_577 H10C C9A 2.9008 no . 2_587 H10C N1A 2.4371 no . 2_587 H10C C10A 2.1176 no . 2_587 H10C H10C 1.8267 no . 2_587 H10C H10D 1.9923 no . 2_587 H10C C11A 3.6471 no . 2_587 H10D C2 3.3935 no . 1_565 H10D C7 2.9239 no . 1_565 H10D C8 2.9383 no . 1_565 H10D C1 3.4741 no . 1_565 H10D H2 2.8813 no . 1_565 H10D C9A 3.2395 no . 2_587 H10D N1A 3.0089 no . 2_587 H10D C10A 2.7565 no . 2_587 H10D H10C 1.9923 no . 2_587 H10D H10D 3.0928 no . 2_587 C11A H15B 3.6748 no . 2_667 C11A H10C 3.6471 no . 2_587 H11C C2 3.6474 no . 2_677 H11C C7 3.1050 no . 2_677 H11C C8 3.4750 no . 2_677 H11C C15 3.5499 no . 2_667 H11C C1 3.2313 no . 2_677 H11C H15A 3.3522 no . 2_667 H11C H15B 3.0680 no . 2_667 H11C H16B 3.1883 no . 2_667 H11C H18A 3.5938 no . 2_667 H11D C2 3.6242 no . 2_577 H11D C5 3.3853 no . 2_577 H11D C6 2.8762 no . 2_577 H11D C7 3.5242 no . 2_577 H11D C18 3.5867 no . 2_667 H11D C1 3.0500 no . 2_577 H11D H6 2.9762 no . 2_577 H11D H15B 3.4019 no . 2_667 H11D H18A 3.0909 no . 2_667 H11D H18B 3.1418 no . 2_667 C13A H17A 3.3479 no . 1_476 C13A H18A 3.6428 no . 2_667 C13A H19B 3.5757 no . 1_476 C13A H19C 2.9857 no . 1_476 H13C C4 3.1926 no . 2_577 H13C C5 3.1451 no . 2_577 H13C C17 3.3546 no . 1_476 H13C C19 3.4760 no . 1_476 H13C H5 3.2282 no . 2_577 H13C H17A 2.5674 no . 1_476 H13C H17B 3.3738 no . 1_476 H13C H18A 2.9165 no . 2_667 H13C H19B 3.5309 no . 1_476 H13C H19C 2.7444 no . 1_476 H13C O1 3.3672 no . 2_577 H13D C2 3.3621 no . 2_677 H13D C4 3.1384 no . 2_677 H13D C5 3.2029 no . 2_677 H13D C6 3.4270 no . 2_677 H13D C19 3.1567 no . 1_476 H13D C1 3.4940 no . 2_677 H13D C3 3.1942 no . 2_677 H13D H3 3.6327 no . 2_677 H13D H5 3.6066 no . 2_677 H13D H16B 3.4961 no . 2_667 H13D H17A 3.5132 no . 1_476 H13D H18A 3.5369 no . 2_667 H13D H19B 3.0717 no . 1_476 H13D H19C 2.4129 no . 1_476 H12C Au1 3.2711 no . 2_587 H12C C2 3.2856 no . 2_577 H12C C4 3.3993 no . 2_577 H12C C1 3.6894 no . 2_577 H12C H2 3.6225 no . 2_577 H12C C3 3.1062 no . 2_577 H12C H3 3.3289 no . 2_577 H12C C9A 3.1405 no . 2_587 H12C N1A 3.5195 no . 2_587 H12D Au1 3.2825 no . 1_565 H12D C2 2.9828 no . 2_677 H12D C8 3.5113 no . 1_565 H12D C1 3.5395 no . 2_677 H12D H2 2.8580 no . 2_677 H12D C3 3.3825 no . 2_677 H12D H3 3.5364 no . 2_677 C14A H6 3.6598 no . 2_587 C14A H15A 3.1604 no . 2_577 C14A H15B 3.5190 no . 2_677 C14A H17A 3.6539 no . 1_476 C14A H17B 3.5489 no . 1_476 C14A H18B 3.0849 no . 2_677 C14A H19B 3.5574 no . 1_476 C14A H19C 3.6373 no . 1_476 H14D C17 3.3873 no . 1_476 H14D C18 3.2900 no . 2_677 H14D C19 3.4052 no . 1_476 H14D C19 3.4437 no . 2_677 H14D H6 3.5684 no . 2_587 H14D H15A 3.4234 no . 2_577 H14D H15B 3.3788 no . 2_677 H14D H16A 3.3877 no . 2_577 H14D H17A 3.1846 no . 1_476 H14D H17B 2.7645 no . 1_476 H14D H17B 3.5273 no . 2_677 H14D H18B 2.5301 no . 2_677 H14D H19A 3.5174 no . 2_677 H14D H19B 2.8281 no . 1_476 H14D H19B 3.0034 no . 2_677 H14D H19C 3.2165 no . 1_476 H14E C4 3.3727 no . 2_577 H14E C8 3.5204 no . 2_587 H14E C15 2.9410 no . 2_577 H14E C16 3.5755 no . 2_577 H14E H3 3.6391 no . 2_577 H14E H6 3.2339 no . 2_587 H14E H15A 2.2311 no . 2_577 H14E H16A 3.2342 no . 2_577 H14E H18B 3.5048 no . 2_677 H14E O1 3.0276 no . 2_577 H14F C4 3.6681 no . 2_677 H14F C15 3.6655 no . 2_677 H14F C3 3.3732 no . 2_677 H14F H3 3.1647 no . 2_677 H14F H6 3.5963 no . 2_587 H14F H15B 2.8164 no . 2_677 H14F H18B 2.8320 no . 2_677 _database_code_depnum_ccdc_archive 'CCDC 927044' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1b #TrackingRef '1.cif' #============================================================================== _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_data_reduction ; CrystalStructure (Molecular Structure Corporation & Rigaku, 2001) ; _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _audit_creation_date 2012-08-16T23:17:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C20 H28 Au1 N1 O1' _chemical_formula_sum 'C20 H28 Au1 N1 O1' _chemical_formula_weight 495.4 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3596(8) _cell_length_b 9.8116(6) _cell_length_c 13.9641(14) _cell_angle_alpha 89.373(7) _cell_angle_beta 88.527(9) _cell_angle_gamma 83.285(6) _cell_volume 1001.06(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.44 _cell_measurement_theta_max 15.59 _cell_measurement_temperature 296 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 13.824 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details '(Coppens et al., 1965)' _exptl_absorpt_correction_T_min 0.1033 _exptl_absorpt_correction_T_max 0.5997 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ? _diffrn_ambient_temperature 296 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Rigaku AFC-5R diffractometer' _diffrn_measurement_method \w _diffrn_reflns_number 4589 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0277 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 70.12 _diffrn_reflns_theta_full 70.12 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measured_fraction_theta_full 0.965 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.46 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3652 _reflns_number_gt 3293 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1246 _refine_ls_goodness_of_fit_ref 1.18 _refine_ls_restrained_S_all 1.17 _refine_ls_number_reflns 3652 _refine_ls_number_parameters 236 _refine_ls_number_restraints 128 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+1.3631P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.77 _refine_diff_density_min -2.075 _refine_diff_density_rms 0.221 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -4.4197 7.298 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.3330(9) -0.2025(7) -0.1105(5) 0.0732(16) Uani d . 1 . . N Au1 0.21922(4) 0.04975(3) 0.02176(2) 0.07000(15) Uani d . 1 . . Au C9 0.2897(11) -0.1096(10) -0.0574(7) 0.080(2) Uani d . 1 . . C O1 0.0007(8) 0.8306(5) 0.3260(4) 0.0768(13) Uani d . 1 . . O C7 0.1225(12) 0.3276(8) 0.1383(7) 0.076(2) Uani d . 1 . . C C8 0.1558(13) 0.2193(10) 0.0965(7) 0.083(2) Uani d . 1 . . C C6 0.0633(10) 0.5774(8) 0.1326(6) 0.0698(17) Uani d . 1 . . C H6 0.0648 0.5734 0.0661 0.084 Uiso calc R 1 . . H C5 0.0356(10) 0.7034(8) 0.1762(6) 0.0674(17) Uani d . 1 . . C H5 0.0213 0.7829 0.1391 0.081 Uiso calc R 1 . . H C10 0.3758(12) -0.3120(8) -0.1751(6) 0.0752(19) Uani d . 1 . . C H10A 0.4854 -0.2974 -0.212 0.09 Uiso calc R 1 . . H H10B 0.2766 -0.3131 -0.2194 0.09 Uiso calc R 1 . . H C12 0.4355(10) -0.5658(8) -0.1947(5) 0.0665(15) Uani d U 1 . . C H12A 0.3297 -0.5625 -0.235 0.08 Uiso calc R 1 . . H H12B 0.5409 -0.5536 -0.2357 0.08 Uiso calc R 1 . . H C2 0.0813(10) 0.4661(7) 0.2849(6) 0.0686(17) Uani d . 1 . . C H2 0.0958 0.3864 0.322 0.082 Uiso calc R 1 . . H C11 0.4059(11) -0.4484(8) -0.1243(5) 0.0682(16) Uani d U 1 . . C H11A 0.3004 -0.4598 -0.0832 0.082 Uiso calc R 1 . . H H11B 0.5118 -0.4504 -0.0842 0.082 Uiso calc R 1 . . H C1 0.0891(10) 0.4559(8) 0.1854(6) 0.0690(18) Uani d . 1 . . C C3 0.0527(11) 0.5911(7) 0.3296(6) 0.0718(18) Uani d . 1 . . C H3 0.0493 0.5951 0.3961 0.086 Uiso calc R 1 . . H C4 0.0287(10) 0.7124(7) 0.2755(6) 0.0659(16) Uani d . 1 . . C C14 0.4869(14) -0.8217(10) -0.2182(8) 0.091(2) Uani d U 1 . . C H14A 0.5051 -0.9074 -0.184 0.137 Uiso calc R 1 . . H H14B 0.5906 -0.8133 -0.2601 0.137 Uiso calc R 1 . . H H14C 0.3785 -0.8187 -0.2553 0.137 Uiso calc R 1 . . H C15 -0.0072(13) 0.9579(8) 0.2724(7) 0.082(2) Uani d U 1 . . C H15A -0.1055 0.9632 0.2271 0.098 Uiso calc R 1 . . H H15B 0.1071 0.9628 0.2371 0.098 Uiso calc R 1 . . H C13 0.4656(11) -0.7047(8) -0.1476(6) 0.0760(18) Uani d U 1 . . C H13A 0.3628 -0.7155 -0.1045 0.091 Uiso calc R 1 . . H H13B 0.5746 -0.7096 -0.1096 0.091 Uiso calc R 1 . . H C16 -0.0398(14) 1.0730(9) 0.3413(8) 0.090(2) Uani d U 1 A . C H16A -0.0248 1.1584 0.308 0.109 Uiso calc R 1 . . H H16B 0.0509 1.0601 0.3908 0.109 Uiso calc R 1 . . H C18 -0.238(2) 1.209(2) 0.4548(17) 0.107(3) Uani d PDU 0.541(15) A 1 C H18A -0.2262 1.2909 0.4167 0.128 Uiso calc PR 0.541(15) A 1 H H18B -0.1365 1.1968 0.498 0.128 Uiso calc PR 0.541(15) A 1 H C19 -0.422(2) 1.233(2) 0.5161(11) 0.112(4) Uani d PDU 0.541(15) A 1 C H19A -0.4311 1.1519 0.5559 0.135 Uiso calc PR 0.541(15) A 1 H H19B -0.4149 1.3094 0.5585 0.135 Uiso calc PR 0.541(15) A 1 H C20 -0.600(2) 1.261(3) 0.4573(18) 0.132(6) Uani d PDU 0.541(15) A 1 C H20A -0.7046 1.2739 0.5004 0.198 Uiso calc PR 0.541(15) A 1 H H20B -0.611 1.1852 0.4162 0.198 Uiso calc PR 0.541(15) A 1 H H20C -0.5953 1.343 0.4192 0.198 Uiso calc PR 0.541(15) A 1 H C18A -0.304(2) 1.209(2) 0.447(2) 0.108(3) Uani d PDU 0.459(15) A 2 C H18C -0.2792 1.2912 0.412 0.13 Uiso calc PR 0.459(15) A 2 H H18D -0.2362 1.207 0.5059 0.13 Uiso calc PR 0.459(15) A 2 H C19A -0.512(2) 1.224(2) 0.474(2) 0.118(4) Uani d PDU 0.459(15) A 2 C H19C -0.5793 1.2106 0.417 0.142 Uiso calc PR 0.459(15) A 2 H H19D -0.5335 1.1502 0.5188 0.142 Uiso calc PR 0.459(15) A 2 H C20A -0.594(3) 1.363(2) 0.521(2) 0.140(7) Uani d PDU 0.459(15) A 2 C H20D -0.7231 1.3612 0.5328 0.21 Uiso calc PR 0.459(15) A 2 H H20E -0.5756 1.4368 0.4775 0.21 Uiso calc PR 0.459(15) A 2 H H20F -0.5349 1.3748 0.5797 0.21 Uiso calc PR 0.459(15) A 2 H C17 -0.2252(14) 1.0829(9) 0.3866(7) 0.098(2) Uani d DU 1 . . C H17A -0.2414 0.9999 0.4226 0.117 Uiso calc PR 0.541(15) A 1 H H17B -0.3183 1.0965 0.3384 0.117 Uiso calc PR 0.541(15) A 1 H H17C -0.2278 1.0045 0.4293 0.117 Uiso d PR 0.459(15) A 2 H H17D -0.3109 1.0722 0.3364 0.117 Uiso d PR 0.459(15) A 2 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.071(4) 0.073(4) 0.075(4) -0.005(3) -0.004(3) -0.015(3) Au1 0.0730(2) 0.0621(2) 0.0753(2) -0.01006(14) 0.00065(14) -0.00236(14) C9 0.062(4) 0.079(5) 0.096(6) -0.003(4) -0.004(4) 0.015(5) O1 0.098(4) 0.053(2) 0.080(3) -0.009(2) -0.007(3) 0.003(2) C7 0.073(5) 0.065(4) 0.092(5) -0.017(3) 0.007(4) -0.014(4) C8 0.080(5) 0.082(5) 0.089(6) -0.023(4) -0.008(4) 0.012(4) C6 0.064(4) 0.074(4) 0.071(4) -0.011(3) 0.001(3) 0.003(3) C5 0.067(4) 0.064(4) 0.071(4) -0.009(3) 0.003(3) 0.008(3) C10 0.082(5) 0.071(4) 0.070(4) 0.000(4) -0.002(4) 0.000(3) C12 0.060(4) 0.076(4) 0.064(3) -0.012(3) 0.003(3) 0.000(3) C2 0.074(4) 0.054(3) 0.080(4) -0.016(3) -0.004(3) 0.005(3) C11 0.064(4) 0.075(4) 0.065(4) -0.005(3) 0.002(3) 0.004(3) C1 0.054(4) 0.074(4) 0.079(4) -0.014(3) 0.007(3) 0.000(4) C3 0.083(5) 0.063(4) 0.071(4) -0.017(3) -0.003(4) 0.004(3) C4 0.065(4) 0.058(4) 0.075(4) -0.007(3) -0.005(3) -0.001(3) C14 0.085(6) 0.075(5) 0.112(7) -0.008(4) 0.006(5) 0.001(4) C15 0.087(5) 0.057(4) 0.102(5) -0.012(3) 0.002(4) 0.007(3) C13 0.069(4) 0.074(4) 0.084(4) -0.008(3) 0.001(3) 0.010(3) C16 0.106(5) 0.062(4) 0.106(5) -0.018(4) -0.007(4) 0.001(3) C18 0.135(8) 0.082(6) 0.102(6) -0.009(6) 0.004(6) -0.005(5) C19 0.137(8) 0.094(6) 0.105(7) -0.007(7) 0.008(6) -0.008(6) C20 0.139(10) 0.120(11) 0.134(11) -0.002(10) 0.000(9) -0.003(10) C18A 0.134(8) 0.085(6) 0.104(7) -0.008(6) 0.005(6) -0.006(5) C19A 0.138(9) 0.099(7) 0.114(8) -0.007(8) 0.012(8) -0.009(7) C20A 0.157(13) 0.119(12) 0.137(14) 0.007(11) 0.018(12) -0.018(11) C17 0.124(6) 0.071(4) 0.097(5) -0.012(4) 0.006(4) -0.002(4) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C9 . 1.191(12) ? N1 C10 . 1.412(10) ? Au1 C9 . 1.937(11) ? Au1 C8 . 1.977(11) ? O1 C4 . 1.356(9) ? O1 C15 . 1.445(9) ? C7 C8 . 1.214(13) ? C7 C1 . 1.419(11) ? C6 C5 . 1.375(11) ? C6 C1 . 1.392(11) ? C6 H6 . 0.93 ? C5 C4 . 1.389(11) ? C5 H5 . 0.93 ? C10 C11 . 1.504(11) ? C10 H10A . 0.97 ? C10 H10B . 0.97 ? C12 C13 . 1.501(11) ? C12 C11 . 1.515(11) ? C12 H12A . 0.97 ? C12 H12B . 0.97 ? C2 C3 . 1.374(10) ? C2 C1 . 1.394(11) ? C2 H2 . 0.93 ? C11 H11A . 0.97 ? C11 H11B . 0.97 ? C3 C4 . 1.398(10) ? C3 H3 . 0.93 ? C14 C13 . 1.514(13) ? C14 H14A . 0.96 ? C14 H14B . 0.96 ? C14 H14C . 0.96 ? C15 C16 . 1.485(12) ? C15 H15A . 0.97 ? C15 H15B . 0.97 ? C13 H13A . 0.97 ? C13 H13B . 0.97 ? C16 C17 . 1.483(13) ? C16 H16A . 0.97 ? C16 H16B . 0.97 ? C18 C17 . 1.563(9) ? C18 C19 . 1.575(9) ? C18 H18A . 0.97 ? C18 H18B . 0.97 ? C19 C20 . 1.564(7) ? C19 H19A . 0.97 ? C19 H19B . 0.97 ? C20 H20A . 0.96 ? C20 H20B . 0.96 ? C20 H20C . 0.96 ? C18A C17 . 1.553(9) ? C18A C19A . 1.562(10) ? C18A H18C . 0.97 ? C18A H18D . 0.97 ? C19A C20A . 1.561(7) ? C19A H19C . 0.97 ? C19A H19D . 0.97 ? C20A H20D . 0.96 ? C20A H20E . 0.96 ? C20A H20F . 0.96 ? C17 H17A . 0.97 ? C17 H17B . 0.97 ? C17 H17C . 0.97 ? C17 H17D . 0.97 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C10 177.3(8) . . ? C9 Au1 C8 176.3(3) . . ? N1 C9 Au1 176.2(8) . . ? C4 O1 C15 117.3(6) . . ? C8 C7 C1 177.9(9) . . ? C7 C8 Au1 176.1(8) . . ? C5 C6 C1 121.7(7) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C6 C5 C4 120.4(7) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? N1 C10 C11 112.0(7) . . ? N1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? N1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C13 C12 C11 113.7(7) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C3 C2 C1 121.5(7) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C10 C11 C12 111.5(6) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108 . . ? C6 C1 C2 117.4(7) . . ? C6 C1 C7 120.5(8) . . ? C2 C1 C7 122.1(8) . . ? C2 C3 C4 120.3(7) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O1 C4 C5 125.4(7) . . ? O1 C4 C3 116.0(7) . . ? C5 C4 C3 118.6(7) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 C16 108.2(8) . . ? O1 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? O1 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C12 C13 C14 113.3(7) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C16 C17 112.3(8) . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C17 C18 C19 114.3(9) . . ? C17 C18 H18A 108.7 . . ? C19 C18 H18A 108.7 . . ? C17 C18 H18B 108.7 . . ? C19 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C20 C19 C18 115.4(9) . . ? C20 C19 H19A 108.4 . . ? C18 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? C18 C19 H19B 108.4 . . ? H19A C19 H19B 107.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C18A C19A 117.6(10) . . ? C17 C18A H18C 107.9 . . ? C19A C18A H18C 107.9 . . ? C17 C18A H18D 107.9 . . ? C19A C18A H18D 107.9 . . ? H18C C18A H18D 107.2 . . ? C20A C19A C18A 116.6(10) . . ? C20A C19A H19C 108.1 . . ? C18A C19A H19C 108.1 . . ? C20A C19A H19D 108.1 . . ? C18A C19A H19D 108.1 . . ? H19C C19A H19D 107.3 . . ? C19A C20A H20D 109.5 . . ? C19A C20A H20E 109.5 . . ? H20D C20A H20E 109.5 . . ? C19A C20A H20F 109.5 . . ? H20D C20A H20F 109.5 . . ? H20E C20A H20F 109.5 . . ? C16 C17 C18A 121.7(10) . . ? C16 C17 C18 105.8(9) . . ? C18A C17 C18 18.3(11) . . ? C16 C17 H17A 110.6 . . ? C18A C17 H17A 108.9 . . ? C18 C17 H17A 110.6 . . ? C16 C17 H17B 110.6 . . ? C18A C17 H17B 94.9 . . ? C18 C17 H17B 110.6 . . ? H17A C17 H17B 108.7 . . ? C16 C17 H17C 107.2 . . ? C18A C17 H17C 105.3 . . ? C18 C17 H17C 104.5 . . ? H17A C17 H17C 8.9 . . ? H17B C17 H17C 117.4 . . ? C16 C17 H17D 107.3 . . ? C18A C17 H17D 107.6 . . ? C18 C17 H17D 124.2 . . ? H17A C17 H17D 98 . . ? H17B C17 H17D 14.2 . . ? H17C C17 H17D 106.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C9 Au1 -7E1(2) . . . . ? C8 Au1 C9 N1 -30(14) . . . . ? C1 C7 C8 Au1 -2E1(4) . . . . ? C9 Au1 C8 C7 1(16) . . . . ? C1 C6 C5 C4 -1.4(12) . . . . ? C9 N1 C10 C11 -109(19) . . . . ? N1 C10 C11 C12 175.1(7) . . . . ? C13 C12 C11 C10 -179.8(7) . . . . ? C5 C6 C1 C2 1.6(11) . . . . ? C5 C6 C1 C7 -178.2(7) . . . . ? C3 C2 C1 C6 -1.2(11) . . . . ? C3 C2 C1 C7 178.6(8) . . . . ? C8 C7 C1 C6 6E1(3) . . . . ? C8 C7 C1 C2 -12E1(3) . . . . ? C1 C2 C3 C4 0.6(12) . . . . ? C15 O1 C4 C5 -5.5(11) . . . . ? C15 O1 C4 C3 174.3(7) . . . . ? C6 C5 C4 O1 -179.4(7) . . . . ? C6 C5 C4 C3 0.7(11) . . . . ? C2 C3 C4 O1 179.8(7) . . . . ? C2 C3 C4 C5 -0.4(12) . . . . ? C4 O1 C15 C16 179.6(7) . . . . ? C11 C12 C13 C14 177.5(7) . . . . ? O1 C15 C16 C17 -68.4(10) . . . . ? C17 C18 C19 C20 -61(2) . . . . ? C17 C18A C19A C20A -170(3) . . . . ? C15 C16 C17 C18A -169.0(18) . . . . ? C15 C16 C17 C18 -179.0(13) . . . . ? C19A C18A C17 C16 168(2) . . . . ? C19A C18A C17 C18 -160(9) . . . . ? C19 C18 C17 C16 -176.1(14) . . . . ? C19 C18 C17 C18A 32(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 927045' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1c #TrackingRef '1.cif' #============================================================================== _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_data_reduction ; CrystalStructure (Molecular Structure Corporation & Rigaku, 2001) ; _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _diffrn_measurement_method \w _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Rigaku AFC-5R diffractometer' _audit_creation_date 2012-08-17T00:01:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic 1c _chemical_formula_moiety 'C21 H30 Au1 N1 O1' _chemical_formula_sum 'C21 H30 Au1 N1 O1' _chemical_formula_weight 509.43 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4166(8) _cell_length_b 9.7574(17) _cell_length_c 14.4580(17) _cell_angle_alpha 90.711(13) _cell_angle_beta 90.313(11) _cell_angle_gamma 97.749(11) _cell_volume 1036.6(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.38 _cell_measurement_theta_max 15.24 _cell_measurement_temperature 296 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.87 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 13.367 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details '(Coppens et al., 1965)' _exptl_absorpt_correction_T_min 0.0303 _exptl_absorpt_correction_T_max 0.4144 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ? _diffrn_ambient_temperature 296 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 4505 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0153 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 70 _diffrn_reflns_theta_full 70 _diffrn_measured_fraction_theta_max 0.96 _diffrn_measured_fraction_theta_full 0.96 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 2 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.84 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3768 _reflns_number_gt 3648 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0994 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.137 _refine_ls_number_reflns 3768 _refine_ls_number_parameters 246 _refine_ls_number_restraints 88 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+1.9676P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.999 _refine_diff_density_min -1.124 _refine_diff_density_rms 0.155 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0121(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -4.4197 7.298 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C14 0.4708(11) 1.8328(8) -0.2197(7) 0.091(2) Uani d . 1 . . C H14A 0.4947 1.9204 -0.188 0.109 Uiso calc R 1 . . H H14B 0.3588 1.8282 -0.2539 0.109 Uiso calc R 1 . . H H14C 0.5685 1.8227 -0.2614 0.109 Uiso calc R 1 . . H C13 0.4555(9) 1.7180(7) -0.1501(5) 0.0745(16) Uani d . 1 . . C H13A 0.5682 1.7247 -0.1149 0.089 Uiso calc R 1 . . H H13B 0.3587 1.7304 -0.1073 0.089 Uiso calc R 1 . . H C12 0.4175(8) 1.5756(7) -0.1933(4) 0.0664(14) Uani d . 1 . . C H12A 0.5164 1.5621 -0.2346 0.08 Uiso calc R 1 . . H H12B 0.3071 1.57 -0.2302 0.08 Uiso calc R 1 . . H C11 0.3961(8) 1.4604(7) -0.1239(4) 0.0666(14) Uani d . 1 . . C H11A 0.506 1.4651 -0.0867 0.08 Uiso calc R 1 . . H H11B 0.296 1.4721 -0.083 0.08 Uiso calc R 1 . . H C10 0.3604(11) 1.3223(7) -0.1708(5) 0.0771(17) Uani d . 1 . . C H10A 0.2578 1.3218 -0.2127 0.092 Uiso calc R 1 . . H H10B 0.4656 1.3083 -0.2075 0.092 Uiso calc R 1 . . H C9 0.2885(9) 1.1213(7) -0.0582(5) 0.0699(15) Uani d . 1 . . C C8 0.1681(10) 0.7826(8) 0.0897(5) 0.0751(16) Uani d U 1 . . C C7 0.1402(8) 0.6745(7) 0.1286(5) 0.0660(14) Uani d U 1 . . C C1 0.1086(7) 0.5433(6) 0.1744(4) 0.0611(13) Uani d . 1 . . C C2 0.0752(8) 0.4198(7) 0.1246(4) 0.0647(14) Uani d . 1 . . C H2 0.0703 0.4224 0.0604 0.078 Uiso calc R 1 . . H C3 0.0491(8) 0.2939(6) 0.1677(4) 0.0602(13) Uani d . 1 . . C H3 0.0278 0.2127 0.1326 0.072 Uiso calc R 1 . . H C4 0.0547(7) 0.2879(6) 0.2632(4) 0.0573(12) Uani d . 1 . . C C5 0.0873(8) 0.4114(6) 0.3147(4) 0.0624(13) Uani d . 1 . . C H5 0.0913 0.4087 0.3789 0.075 Uiso calc R 1 . . H C6 0.1133(8) 0.5353(6) 0.2710(4) 0.0618(13) Uani d . 1 . . C H6 0.1346 0.6164 0.3061 0.074 Uiso calc R 1 . . H C15 0.0144(10) 0.0403(6) 0.2633(5) 0.0722(15) Uani d U 1 . . C H15A 0.1223 0.0351 0.2265 0.087 Uiso calc R 1 . . H H15B -0.0902 0.0324 0.2221 0.087 Uiso calc R 1 . . H C16 -0.0080(10) -0.0734(7) 0.3312(6) 0.0813(18) Uani d U 1 . . C H16A 0.0893 -0.0572 0.3768 0.098 Uiso calc R 1 . . H H16B 0.0034 -0.1598 0.2993 0.098 Uiso calc R 1 . . H C17 -0.1923(11) -0.0876(8) 0.3815(6) 0.0892(19) Uani d U 1 A . C H17A -0.2005 -0.0036 0.417 0.107 Uiso calc R 1 . . H H17B -0.2899 -0.0979 0.336 0.107 Uiso calc R 1 . . H C18 -0.2173(11) -0.2094(10) 0.4453(7) 0.112(3) Uani d DU 1 . . C H18A -0.1459 -0.1927 0.5018 0.135 Uiso calc PR 0.278(12) A 1 H H18B -0.1916 -0.2941 0.4154 0.135 Uiso calc PR 0.278(12) A 1 H H18C -0.115 -0.201 0.4881 0.135 Uiso d PR 0.722(12) A 2 H H18D -0.2195 -0.2947 0.41 0.135 Uiso d PR 0.722(12) A 2 H C20 -0.506(3) -0.344(3) 0.507(2) 0.106(3) Uani d PDU 0.278(12) A 1 C H20A -0.4313 -0.3618 0.5598 0.127 Uiso calc PR 0.278(12) A 1 H H20B -0.5066 -0.4196 0.4632 0.127 Uiso calc PR 0.278(12) A 1 H C21 -0.701(3) -0.334(5) 0.539(3) 0.107(5) Uani d PDU 0.278(12) A 1 C H21A -0.7509 -0.4191 0.5669 0.129 Uiso calc PR 0.278(12) A 1 H H21B -0.7744 -0.316 0.4869 0.129 Uiso calc PR 0.278(12) A 1 H H21C -0.6994 -0.2596 0.5836 0.129 Uiso calc PR 0.278(12) A 1 H C19 -0.424(2) -0.208(3) 0.462(3) 0.105(4) Uani d PDU 0.278(12) A 1 C H19A -0.4422 -0.1304 0.5015 0.126 Uiso calc PR 0.278(12) A 1 H H19B -0.4853 -0.1979 0.4033 0.126 Uiso calc PR 0.278(12) A 1 H C19A -0.3831(12) -0.2272(15) 0.5080(7) 0.104(3) Uani d PDU 0.722(12) A 2 C H19C -0.395 -0.1403 0.5391 0.125 Uiso calc PR 0.722(12) A 2 H H19D -0.3689 -0.2956 0.5546 0.125 Uiso calc PR 0.722(12) A 2 H C20A -0.5532(11) -0.2740(15) 0.4494(7) 0.105(3) Uani d PDU 0.722(12) A 2 C H20C -0.5317 -0.3507 0.4096 0.126 Uiso calc PR 0.722(12) A 2 H H20D -0.5791 -0.1987 0.4105 0.126 Uiso calc PR 0.722(12) A 2 H C21A -0.7169(14) -0.319(2) 0.5115(10) 0.110(3) Uani d PDU 0.722(12) A 2 C H21D -0.8219 -0.349 0.4737 0.132 Uiso calc PR 0.722(12) A 2 H H21E -0.7403 -0.2418 0.5496 0.132 Uiso calc PR 0.722(12) A 2 H H21F -0.6911 -0.3931 0.5501 0.132 Uiso calc PR 0.722(12) A 2 H N1 0.3221(7) 1.2080(6) -0.1073(4) 0.0722(13) Uani d . 1 . . N O1 0.0313(6) 0.1698(4) 0.3132(3) 0.0687(10) Uani d . 1 . . O Au1 0.22475(3) 0.95505(2) 0.018157(17) 0.06737(18) Uani d . 1 . . Au loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C14 0.078(4) 0.072(4) 0.123(7) 0.011(3) 0.003(4) -0.004(4) C13 0.062(3) 0.075(4) 0.087(4) 0.012(3) 0.004(3) -0.012(3) C12 0.061(3) 0.072(4) 0.067(3) 0.009(3) 0.005(3) 0.001(3) C11 0.059(3) 0.079(4) 0.060(3) 0.005(3) 0.002(2) -0.002(3) C10 0.089(4) 0.075(4) 0.066(4) 0.004(3) 0.000(3) 0.010(3) C9 0.068(4) 0.067(4) 0.073(4) 0.003(3) 0.001(3) 0.001(3) C8 0.078(4) 0.078(4) 0.070(4) 0.013(3) 0.005(3) -0.005(3) C7 0.066(3) 0.064(3) 0.069(3) 0.010(3) 0.009(3) 0.013(3) C1 0.053(3) 0.066(3) 0.066(3) 0.014(2) 0.005(2) 0.008(3) C2 0.066(3) 0.075(4) 0.054(3) 0.012(3) 0.003(2) -0.001(3) C3 0.063(3) 0.060(3) 0.057(3) 0.008(2) 0.002(2) -0.006(2) C4 0.055(3) 0.056(3) 0.061(3) 0.010(2) 0.004(2) 0.001(2) C5 0.069(3) 0.063(3) 0.056(3) 0.013(3) 0.002(2) -0.005(2) C6 0.066(3) 0.056(3) 0.064(3) 0.011(2) -0.001(2) -0.003(2) C15 0.079(4) 0.055(3) 0.083(4) 0.011(3) 0.013(3) -0.007(3) C16 0.092(4) 0.058(4) 0.095(5) 0.013(3) 0.013(4) 0.002(3) C17 0.098(5) 0.073(4) 0.096(5) 0.013(4) 0.015(4) -0.001(3) C18 0.123(6) 0.086(5) 0.125(7) 0.001(5) 0.031(5) 0.013(5) C20 0.108(6) 0.123(7) 0.086(7) 0.009(5) 0.010(5) 0.006(6) C21 0.105(7) 0.128(9) 0.089(10) 0.013(7) 0.007(7) 0.003(8) C19 0.114(6) 0.119(8) 0.081(8) 0.009(6) 0.010(6) 0.008(7) C19A 0.113(6) 0.117(7) 0.079(6) 0.004(5) 0.009(4) 0.010(5) C20A 0.108(5) 0.123(6) 0.083(6) 0.016(5) 0.007(4) 0.004(5) C21A 0.107(5) 0.131(7) 0.091(7) 0.014(5) 0.008(5) -0.003(6) N1 0.067(3) 0.070(3) 0.079(3) 0.007(2) 0.000(2) 0.006(3) O1 0.088(3) 0.054(2) 0.063(2) 0.0078(19) 0.0069(19) 0.0003(17) Au1 0.0773(2) 0.0603(2) 0.0648(2) 0.00963(12) 0.00368(12) 0.00346(11) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C14 C13 . 1.508(12) ? C14 H14A . 0.96 ? C14 H14B . 0.96 ? C14 H14C . 0.96 ? C13 C12 . 1.507(9) ? C13 H13A . 0.97 ? C13 H13B . 0.97 ? C12 C11 . 1.508(9) ? C12 H12A . 0.97 ? C12 H12B . 0.97 ? C11 C10 . 1.491(10) ? C11 H11A . 0.97 ? C11 H11B . 0.97 ? C10 N1 . 1.453(9) ? C10 H10A . 0.97 ? C10 H10B . 0.97 ? C9 N1 . 1.114(9) ? C9 Au1 . 1.979(7) ? C8 C7 . 1.196(10) ? C8 Au1 . 1.984(8) ? C7 C1 . 1.440(9) ? C1 C2 . 1.388(9) ? C1 C6 . 1.400(8) ? C2 C3 . 1.375(9) ? C2 H2 . 0.93 ? C3 C4 . 1.384(8) ? C3 H3 . 0.93 ? C4 O1 . 1.360(7) ? C4 C5 . 1.400(8) ? C5 C6 . 1.362(8) ? C5 H5 . 0.93 ? C6 H6 . 0.93 ? C15 O1 . 1.437(7) ? C15 C16 . 1.483(10) ? C15 H15A . 0.97 ? C15 H15B . 0.97 ? C16 C17 . 1.542(10) ? C16 H16A . 0.97 ? C16 H16B . 0.97 ? C17 C18 . 1.506(12) ? C17 H17A . 0.97 ? C17 H17B . 0.97 ? C18 C19A . 1.523(8) ? C18 C19 . 1.556(10) ? C18 H18A . 0.97 ? C18 H18B . 0.97 ? C18 H18C . 0.97 ? C18 H18D . 0.97 ? C20 C19 . 1.533(10) ? C20 C21 . 1.537(10) ? C20 H20A . 0.97 ? C20 H20B . 0.97 ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? C19 H19A . 0.97 ? C19 H19B . 0.97 ? C19A C20A . 1.530(9) ? C19A H19C . 0.97 ? C19A H19D . 0.97 ? C20A C21A . 1.532(8) ? C20A H20C . 0.97 ? C20A H20D . 0.97 ? C21A H21D . 0.96 ? C21A H21E . 0.96 ? C21A H21F . 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C13 C14 113.5(6) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C12 C11 113.8(6) . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C10 C11 C12 111.3(5) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? N1 C10 C11 113.7(6) . . ? N1 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? N1 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? N1 C9 Au1 174.3(6) . . ? C7 C8 Au1 175.7(6) . . ? C8 C7 C1 179.0(7) . . ? C2 C1 C6 117.4(6) . . ? C2 C1 C7 121.4(6) . . ? C6 C1 C7 121.2(6) . . ? C3 C2 C1 121.8(6) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 120.0(5) . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? O1 C4 C3 125.2(5) . . ? O1 C4 C5 115.8(5) . . ? C3 C4 C5 119.1(5) . . ? C6 C5 C4 120.3(6) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 121.4(6) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? O1 C15 C16 108.4(6) . . ? O1 C15 H15A 110 . . ? C16 C15 H15A 110 . . ? O1 C15 H15B 110 . . ? C16 C15 H15B 110 . . ? H15A C15 H15B 108.4 . . ? C15 C16 C17 113.3(6) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 112.4(7) . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C19A 118.4(9) . . ? C17 C18 C19 96.3(9) . . ? C19A C18 C19 28.9(11) . . ? C17 C18 H18A 112.5 . . ? C19A C18 H18A 86 . . ? C19 C18 H18A 112.5 . . ? C17 C18 H18B 112.5 . . ? C19A C18 H18B 114.4 . . ? C19 C18 H18B 112.5 . . ? H18A C18 H18B 110 . . ? C17 C18 H18C 108.4 . . ? C19A C18 H18C 103.9 . . ? C19 C18 H18C 131.3 . . ? H18A C18 H18C 19.1 . . ? H18B C18 H18C 96.1 . . ? C17 C18 H18D 110 . . ? C19A C18 H18D 107 . . ? C19 C18 H18D 100.7 . . ? H18A C18 H18D 121.4 . . ? H18B C18 H18D 13 . . ? H18C C18 H18D 108.7 . . ? C19 C20 C21 110.2(10) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C19 C18 109.7(9) . . ? C20 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? C20 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C18 C19A C20A 109.1(7) . . ? C18 C19A H19C 109.9 . . ? C20A C19A H19C 109.9 . . ? C18 C19A H19D 109.9 . . ? C20A C19A H19D 109.9 . . ? H19C C19A H19D 108.3 . . ? C19A C20A C21A 110.6(7) . . ? C19A C20A H20C 109.5 . . ? C21A C20A H20C 109.5 . . ? C19A C20A H20D 109.5 . . ? C21A C20A H20D 109.5 . . ? H20C C20A H20D 108.1 . . ? C20A C21A H21D 109.5 . . ? C20A C21A H21E 109.5 . . ? H21D C21A H21E 109.5 . . ? C20A C21A H21F 109.5 . . ? H21D C21A H21F 109.5 . . ? H21E C21A H21F 109.5 . . ? C9 N1 C10 178.2(7) . . ? C4 O1 C15 117.7(5) . . ? C9 Au1 C8 176.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C13 C12 C11 -178.1(6) . . . . ? C13 C12 C11 C10 -179.5(6) . . . . ? C12 C11 C10 N1 -174.7(6) . . . . ? Au1 C8 C7 C1 0E1(6) . . . . ? C8 C7 C1 C2 -4E1(5) . . . . ? C8 C7 C1 C6 14E1(5) . . . . ? C6 C1 C2 C3 -0.6(9) . . . . ? C7 C1 C2 C3 178.4(6) . . . . ? C1 C2 C3 C4 0.4(9) . . . . ? C2 C3 C4 O1 -179.9(5) . . . . ? C2 C3 C4 C5 -0.1(8) . . . . ? O1 C4 C5 C6 179.7(5) . . . . ? C3 C4 C5 C6 0.0(8) . . . . ? C4 C5 C6 C1 -0.1(9) . . . . ? C2 C1 C6 C5 0.4(8) . . . . ? C7 C1 C6 C5 -178.6(6) . . . . ? O1 C15 C16 C17 69.2(8) . . . . ? C15 C16 C17 C18 176.2(8) . . . . ? C16 C17 C18 C19A 173.1(8) . . . . ? C16 C17 C18 C19 -167.3(16) . . . . ? C21 C20 C19 C18 170(3) . . . . ? C17 C18 C19 C20 166(3) . . . . ? C19A C18 C19 C20 -51(2) . . . . ? C17 C18 C19A C20A 72.4(14) . . . . ? C19 C18 C19A C20A 29(2) . . . . ? C18 C19A C20A C21A 169.6(14) . . . . ? Au1 C9 N1 C10 10E1(2) . . . . ? C11 C10 N1 C9 7E1(2) . . . . ? C3 C4 O1 C15 5.4(8) . . . . ? C5 C4 O1 C15 -174.3(5) . . . . ? C16 C15 O1 C4 179.5(5) . . . . ? N1 C9 Au1 C8 38(9) . . . . ? C7 C8 Au1 C9 1(12) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 927046' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1d #TrackingRef '1.cif' #============================================================================== _diffrn_measurement_method \w _diffrn_measurement_device_type 'Rigaku AFC-5R diffractometer' _audit_creation_date 2012-08-17T00:59:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #============================================================================== # CHEMICAL DATA _chemical_name_systematic 1d _chemical_formula_moiety 'C22 H32 Au1 N1 O1' _chemical_formula_sum 'C22 H32 Au1 N1 O1' _chemical_formula_weight 523.45 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9221(16) _cell_length_b 9.6174(11) _cell_length_c 13.6118(19) _cell_angle_alpha 76.298(10) _cell_angle_beta 77.979(13) _cell_angle_gamma 87.684(13) _cell_volume 1109.8(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 9.33 _cell_measurement_theta_max 17.04 _cell_measurement_temperature 296 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 12.502 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.454 _exptl_absorpt_correction_T_max 0.606 #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ? _diffrn_ambient_temperature 296 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_monochromator graphite _diffrn_reflns_number 4910 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_unetI/netI 0.0833 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 70.06 _diffrn_reflns_theta_full 70.06 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measured_fraction_theta_full 0.959 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 7.37 #============================================================================== # STRUCTURE SOLUTION _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 4049 _reflns_number_gt 2566 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.098 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.132 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 0.995 _refine_ls_number_constraints 4049 _refine_ls_number_reflns 4049 _refine_ls_number_parameters 282 _refine_ls_number_restraints 227 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.52 _refine_diff_density_min -0.954 _refine_diff_density_rms 0.121 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00102(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -4.4197 7.298 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_reduction 'CrystalStructure (Molecular Structure Corporation & Rigaku, 2001)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ;ORTEP-3 for Windows (Farrugia, 1997) and VESTA (Momma & Izumi, 2008) ; _computing_publication_material 'WinGX (Farrugia, 1999)' #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Au1 0.16194(5) 0.21151(5) 0.44249(4) 0.07452(19) Uani d U 1 . . Au C9 -0.0252(13) 0.1800(11) 0.3955(9) 0.080(2) Uani d U 1 . . C C7 0.4632(12) 0.2374(10) 0.5250(8) 0.074(2) Uani d U 1 . . C N1 -0.1310(11) 0.1530(10) 0.3668(8) 0.091(2) Uani d U 1 . . N O1 0.9721(8) 0.2379(7) 0.7060(6) 0.0811(19) Uani d . 1 . . O C8 0.3516(12) 0.2307(11) 0.4904(9) 0.078(2) Uani d U 1 . . C C16 1.1863(12) 0.3270(11) 0.7508(9) 0.0829(18) Uani d U 1 . . C H16A 1.2521 0.2595 0.7197 0.099 Uiso calc RU 1 . . H H16B 1.1439 0.2791 0.8218 0.099 Uiso calc R 1 . . H C18 1.4180(12) 0.4124(12) 0.8047(9) 0.0837(19) Uani d U 1 A . C H18A 1.3801 0.3578 0.8747 0.1 Uiso calc R 1 . . H H18B 1.4869 0.3514 0.7688 0.1 Uiso calc R 1 . . H C17 1.2827(12) 0.4518(11) 0.7508(9) 0.0822(18) Uani d U 1 . . C H17A 1.2177 0.5175 0.7842 0.099 Uiso calc R 1 . . H H17B 1.3219 0.5018 0.6797 0.099 Uiso calc R 1 . . H C3 0.7976(12) 0.3721(10) 0.6020(8) 0.070(3) Uani d . 1 . . C H3 0.849 0.458 0.5924 0.085 Uiso calc R 1 . . H C1 0.5970(11) 0.2430(10) 0.5678(8) 0.070(3) Uani d . 1 . . C C5 0.7730(12) 0.1220(10) 0.6685(8) 0.078(3) Uani d . 1 . . C H5 0.8061 0.0373 0.7068 0.093 Uiso calc R 1 . . H C15 1.0576(12) 0.3653(11) 0.6946(9) 0.081(2) Uani d U 1 . . C H15A 0.9919 0.4351 0.7231 0.097 Uiso calc R 1 . . H H15B 1.0979 0.4067 0.622 0.097 Uiso calc R 1 . . H C6 0.6514(12) 0.1178(11) 0.6235(9) 0.077(3) Uani d . 1 . . C H6 0.6042 0.0306 0.63 0.092 Uiso calc R 1 . . H C2 0.6725(11) 0.3715(10) 0.5592(8) 0.069(2) Uani d . 1 . . C H2 0.637 0.4571 0.5239 0.083 Uiso calc R 1 . . H C10 -0.2513(14) 0.1150(14) 0.3247(10) 0.100(2) Uani d U 1 B . C H10A -0.3334 0.1838 0.3297 0.12 Uiso calc R 1 . . H H10B -0.292 0.0215 0.3635 0.12 Uiso calc R 1 . . H C4 0.8496(11) 0.2489(11) 0.6591(7) 0.069(2) Uani d . 1 . . C C20 1.650(5) 0.528(4) 0.856(6) 0.090(3) Uani d PDU 0.26(5) A 1 C H20A 1.7372 0.5024 0.8076 0.108 Uiso calc PR 0.26(5) A 1 H H20B 1.6346 0.4532 0.9187 0.108 Uiso calc PR 0.26(5) A 1 H C21 1.684(6) 0.671(4) 0.880(5) 0.094(6) Uani d PDU 0.26(5) A 1 C H21A 1.6028 0.6906 0.9341 0.113 Uiso calc PR 0.26(5) A 1 H H21B 1.6873 0.7478 0.8187 0.113 Uiso calc PR 0.26(5) A 1 H C22 1.839(4) 0.662(8) 0.914(4) 0.096(9) Uani d PDU 0.26(5) A 1 C H22A 1.8653 0.7549 0.9207 0.116 Uiso calc PR 0.26(5) A 1 H H22B 1.9165 0.6317 0.8637 0.116 Uiso calc PR 0.26(5) A 1 H H22C 1.8304 0.595 0.9796 0.116 Uiso calc PR 0.26(5) A 1 H C20A 1.638(2) 0.489(2) 0.8664(18) 0.090(2) Uani d PDU 0.74(5) A 2 C H20C 1.5955 0.4362 0.9362 0.108 Uiso calc PR 0.74(5) A 2 H H20D 1.7042 0.4254 0.8316 0.108 Uiso calc PR 0.74(5) A 2 H C21A 1.732(2) 0.617(3) 0.8701(15) 0.106(7) Uani d PDU 0.74(5) A 2 C H21C 1.7768 0.6681 0.8003 0.128 Uiso calc PR 0.74(5) A 2 H H21D 1.6641 0.6828 0.9025 0.128 Uiso calc PR 0.74(5) A 2 H C22A 1.8584(19) 0.569(5) 0.9308(16) 0.117(8) Uani d PDU 0.74(5) A 2 C H22D 1.9187 0.6509 0.9285 0.14 Uiso calc PR 0.74(5) A 2 H H22E 1.9227 0.5016 0.9006 0.14 Uiso calc PR 0.74(5) A 2 H H22F 1.8133 0.5255 1.0013 0.14 Uiso calc PR 0.74(5) A 2 H C19 1.5066(11) 0.5403(12) 0.8085(9) 0.088(2) Uani d DU 1 . . C H19A 1.4344 0.5984 0.8449 0.106 Uiso calc PR 0.26(5) A 1 H H19B 1.5366 0.5955 0.7379 0.106 Uiso calc PR 0.26(5) A 1 H H19C 1.4406 0.603 0.8445 0.106 Uiso d PR 0.74(5) A 2 H H19D 1.5499 0.5941 0.7392 0.106 Uiso d PR 0.74(5) A 2 H C12 -0.314(3) 0.052(4) 0.1690(16) 0.118(3) Uani d PDU 0.406(13) B 3 C H12A -0.4129 0.0502 0.2156 0.142 Uiso calc PR 0.406(13) B 3 H H12B -0.289 -0.0459 0.1641 0.142 Uiso calc PR 0.406(13) B 3 H C13 -0.324(3) 0.144(4) 0.0614(15) 0.123(3) Uani d PDU 0.406(13) B 3 C H13A -0.4156 0.1184 0.0417 0.147 Uiso calc PR 0.406(13) B 3 H H13B -0.331 0.2442 0.0639 0.147 Uiso calc PR 0.406(13) B 3 H C14 -0.184(4) 0.123(4) -0.0189(19) 0.126(3) Uani d PDU 0.406(13) B 3 C H14A -0.1851 0.1905 -0.0831 0.151 Uiso calc PR 0.406(13) B 3 H H14B -0.1852 0.0273 -0.029 0.151 Uiso calc PR 0.406(13) B 3 H H14C -0.0926 0.1368 0.0046 0.151 Uiso calc PR 0.406(13) B 3 H C12A -0.3137(18) 0.077(3) 0.1570(12) 0.119(3) Uani d PDU 0.594(13) B 4 C H12C -0.3846 0.1558 0.1479 0.143 Uiso calc PR 0.594(13) B 4 H H12D -0.3711 -0.0078 0.1984 0.143 Uiso calc PR 0.594(13) B 4 H C13A -0.234(2) 0.051(3) 0.0507(13) 0.123(3) Uani d PDU 0.594(13) B 4 C H13C -0.1594 0.1263 0.0158 0.148 Uiso calc PR 0.594(13) B 4 H H13D -0.1811 -0.0396 0.0602 0.148 Uiso calc PR 0.594(13) B 4 H C14A -0.353(3) 0.049(3) -0.0155(14) 0.126(3) Uani d PDU 0.594(13) B 4 C H14D -0.3009 0.0531 -0.0855 0.151 Uiso calc PR 0.594(13) B 4 H H14E -0.4187 0.1298 -0.0135 0.151 Uiso calc PR 0.594(13) B 4 H H14F -0.4123 -0.0378 0.011 0.151 Uiso calc PR 0.594(13) B 4 H C11 -0.1916(15) 0.1119(14) 0.2120(9) 0.112(2) Uani d DU 1 . . C H11A -0.1008 0.053 0.2062 0.134 Uiso calc PR 0.406(13) B 3 H H11B -0.1632 0.2081 0.1717 0.134 Uiso calc PR 0.406(13) B 3 H H11C -0.099 0.0553 0.2071 0.134 Uiso d PR 0.594(13) B 4 H H11D -0.1635 0.2087 0.1728 0.134 Uiso d PR 0.594(13) B 4 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Au1 0.0785(3) 0.0686(3) 0.0789(3) 0.0020(2) -0.0200(2) -0.01896(19) C9 0.081(6) 0.073(5) 0.083(6) 0.001(5) -0.017(5) -0.010(5) C7 0.069(6) 0.063(5) 0.087(6) 0.004(5) -0.013(5) -0.017(5) N1 0.088(5) 0.086(4) 0.097(5) 0.000(4) -0.028(4) -0.011(4) O1 0.083(5) 0.070(4) 0.093(5) -0.002(4) -0.029(4) -0.013(4) C8 0.079(6) 0.067(5) 0.091(7) 0.001(5) -0.017(5) -0.024(5) C16 0.078(4) 0.090(4) 0.083(4) 0.006(3) -0.021(3) -0.022(3) C18 0.078(4) 0.096(4) 0.078(4) 0.002(3) -0.017(3) -0.020(4) C17 0.078(4) 0.090(4) 0.079(4) 0.004(3) -0.020(3) -0.019(4) C3 0.078(7) 0.057(5) 0.075(6) -0.005(5) -0.006(5) -0.020(5) C1 0.067(6) 0.065(6) 0.080(7) 0.001(5) -0.014(5) -0.022(5) C5 0.083(7) 0.059(6) 0.080(7) -0.003(5) -0.009(6) 0.000(5) C15 0.076(5) 0.088(5) 0.082(5) 0.007(4) -0.020(4) -0.025(4) C6 0.074(7) 0.068(6) 0.088(7) -0.004(5) -0.015(6) -0.020(5) C2 0.068(6) 0.066(6) 0.076(6) 0.006(5) -0.015(5) -0.025(5) C10 0.098(5) 0.096(5) 0.105(5) -0.002(4) -0.035(4) -0.010(4) C4 0.072(6) 0.075(6) 0.062(6) 0.002(5) -0.020(5) -0.017(5) C20 0.081(5) 0.107(6) 0.081(6) -0.007(5) -0.017(4) -0.018(5) C21 0.085(10) 0.112(10) 0.083(11) -0.007(10) -0.013(10) -0.023(9) C22 0.082(16) 0.12(2) 0.090(19) -0.014(16) -0.007(14) -0.029(17) C20A 0.080(5) 0.108(6) 0.082(5) -0.008(5) -0.017(4) -0.017(5) C21A 0.081(11) 0.161(19) 0.084(10) -0.042(11) -0.010(9) -0.040(11) C22A 0.085(11) 0.16(2) 0.102(12) -0.021(12) -0.012(8) -0.034(13) C19 0.081(4) 0.103(5) 0.080(5) -0.005(4) -0.018(4) -0.018(4) C12 0.131(6) 0.119(6) 0.110(5) 0.004(5) -0.045(5) -0.018(5) C13 0.136(6) 0.124(6) 0.111(5) 0.006(5) -0.045(5) -0.017(5) C14 0.139(7) 0.128(7) 0.112(6) 0.007(6) -0.042(5) -0.016(5) C12A 0.131(6) 0.119(6) 0.110(5) 0.005(5) -0.044(5) -0.017(5) C13A 0.136(6) 0.124(6) 0.110(5) 0.007(5) -0.043(5) -0.018(5) C14A 0.140(7) 0.128(7) 0.112(6) 0.007(6) -0.043(5) -0.018(5) C11 0.121(5) 0.109(5) 0.108(5) 0.004(4) -0.040(4) -0.017(4) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Au1 C8 . 1.966(11) ? Au1 C9 . 1.966(12) ? C9 N1 . 1.155(13) ? C7 C8 . 1.197(14) ? C7 C1 . 1.442(14) ? N1 C10 . 1.414(14) ? O1 C4 . 1.365(11) ? O1 C15 . 1.430(12) ? C16 C15 . 1.495(13) ? C16 C17 . 1.504(14) ? C16 H16A . 0.97 ? C16 H16B . 0.97 ? C18 C19 . 1.506(13) ? C18 C17 . 1.530(14) ? C18 H18A . 0.97 ? C18 H18B . 0.97 ? C17 H17A . 0.97 ? C17 H17B . 0.97 ? C3 C2 . 1.364(13) ? C3 C4 . 1.376(13) ? C3 H3 . 0.93 ? C1 C6 . 1.390(13) ? C1 C2 . 1.400(12) ? C5 C6 . 1.359(14) ? C5 C4 . 1.389(13) ? C5 H5 . 0.93 ? C15 H15A . 0.97 ? C15 H15B . 0.97 ? C6 H6 . 0.93 ? C2 H2 . 0.93 ? C10 C11 . 1.523(17) ? C10 H10A . 0.97 ? C10 H10B . 0.97 ? C20 C19 . 1.536(10) ? C20 C21 . 1.537(10) ? C20 H20A . 0.97 ? C20 H20B . 0.97 ? C21 C22 . 1.541(10) ? C21 H21A . 0.97 ? C21 H21B . 0.97 ? C22 H22A . 0.96 ? C22 H22B . 0.96 ? C22 H22C . 0.96 ? C20A C21A . 1.534(9) ? C20A C19 . 1.546(9) ? C20A H20C . 0.97 ? C20A H20D . 0.97 ? C21A C22A . 1.530(9) ? C21A H21C . 0.97 ? C21A H21D . 0.97 ? C22A H22D . 0.96 ? C22A H22E . 0.96 ? C22A H22F . 0.96 ? C19 H19A . 0.97 ? C19 H19B . 0.97 ? C19 H19C . 0.97 ? C19 H19D . 0.97 ? C12 C11 . 1.535(10) ? C12 C13 . 1.540(10) ? C12 H12A . 0.97 ? C12 H12B . 0.97 ? C13 C14 . 1.522(10) ? C13 H13A . 0.97 ? C13 H13B . 0.97 ? C14 H14A . 0.96 ? C14 H14B . 0.96 ? C14 H14C . 0.96 ? C12A C11 . 1.532(9) ? C12A C13A . 1.545(10) ? C12A H12C . 0.97 ? C12A H12D . 0.97 ? C13A C14A . 1.526(9) ? C13A H13C . 0.97 ? C13A H13D . 0.97 ? C14A H14D . 0.96 ? C14A H14E . 0.96 ? C14A H14F . 0.96 ? C11 H11A . 0.97 ? C11 H11B . 0.97 ? C11 H11C . 0.97 ? C11 H11D . 0.97 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 Au1 C9 176.6(4) . . ? N1 C9 Au1 175.5(10) . . ? C8 C7 C1 179.0(12) . . ? C9 N1 C10 174.8(12) . . ? C4 O1 C15 117.9(8) . . ? C7 C8 Au1 176.2(11) . . ? C15 C16 C17 114.8(9) . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? C17 C16 H16B 108.6 . . ? H16A C16 H16B 107.5 . . ? C19 C18 C17 113.5(9) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C16 C17 C18 114.9(9) . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C2 C3 C4 121.7(9) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C6 C1 C2 117.9(9) . . ? C6 C1 C7 119.6(9) . . ? C2 C1 C7 122.5(9) . . ? C6 C5 C4 122.0(10) . . ? C6 C5 H5 119 . . ? C4 C5 H5 119 . . ? O1 C15 C16 108.3(9) . . ? O1 C15 H15A 110 . . ? C16 C15 H15A 110 . . ? O1 C15 H15B 110 . . ? C16 C15 H15B 110 . . ? H15A C15 H15B 108.4 . . ? C5 C6 C1 120.4(10) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C3 C2 C1 120.6(9) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? N1 C10 C11 109.7(10) . . ? N1 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? N1 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O1 C4 C3 126.4(9) . . ? O1 C4 C5 116.2(9) . . ? C3 C4 C5 117.4(9) . . ? C19 C20 C21 110.6(10) . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C20 C21 C22 109.9(10) . . ? C20 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? C20 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21A C20A C19 110.4(8) . . ? C21A C20A H20C 109.6 . . ? C19 C20A H20C 109.6 . . ? C21A C20A H20D 109.6 . . ? C19 C20A H20D 109.6 . . ? H20C C20A H20D 108.1 . . ? C22A C21A C20A 111.2(9) . . ? C22A C21A H21C 109.4 . . ? C20A C21A H21C 109.4 . . ? C22A C21A H21D 109.4 . . ? C20A C21A H21D 109.4 . . ? H21C C21A H21D 108 . . ? C21A C22A H22D 109.5 . . ? C21A C22A H22E 109.5 . . ? H22D C22A H22E 109.5 . . ? C21A C22A H22F 109.5 . . ? H22D C22A H22F 109.5 . . ? H22E C22A H22F 109.5 . . ? C18 C19 C20 123.2(17) . . ? C18 C19 C20A 109.3(10) . . ? C20 C19 C20A 14.2(18) . . ? C18 C19 H19A 106.5 . . ? C20 C19 H19A 106.5 . . ? C20A C19 H19A 111.1 . . ? C18 C19 H19B 106.5 . . ? C20 C19 H19B 106.5 . . ? C20A C19 H19B 116.4 . . ? H19A C19 H19B 106.5 . . ? C18 C19 H19C 110.7 . . ? C20 C19 H19C 103.5 . . ? C20A C19 H19C 108.8 . . ? H19A C19 H19C 4.2 . . ? H19B C19 H19C 105.1 . . ? C18 C19 H19D 110.4 . . ? C20 C19 H19D 99.3 . . ? C20A C19 H19D 109.1 . . ? H19A C19 H19D 110.5 . . ? H19B C19 H19D 7.3 . . ? H19C C19 H19D 108.6 . . ? C11 C12 C13 110.3(10) . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 110.9(10) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C12A C13A 109.1(9) . . ? C11 C12A H12C 109.9 . . ? C13A C12A H12C 109.9 . . ? C11 C12A H12D 109.9 . . ? C13A C12A H12D 109.9 . . ? H12C C12A H12D 108.3 . . ? C14A C13A C12A 110.3(9) . . ? C14A C13A H13C 109.6 . . ? C12A C13A H13C 109.6 . . ? C14A C13A H13D 109.6 . . ? C12A C13A H13D 109.6 . . ? H13C C13A H13D 108.1 . . ? C13A C14A H14D 109.5 . . ? C13A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C13A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? C10 C11 C12A 114.4(10) . . ? C10 C11 C12 110.5(14) . . ? C12A C11 C12 9.7(19) . . ? C10 C11 H11A 109.5 . . ? C12A C11 H11A 114.7 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12A C11 H11B 99.9 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C10 C11 H11C 108.7 . . ? C12A C11 H11C 116.6 . . ? C12 C11 H11C 111.5 . . ? H11A C11 H11C 1.9 . . ? H11B C11 H11C 107 . . ? C10 C11 H11D 108.6 . . ? C12A C11 H11D 100.6 . . ? C12 C11 H11D 110.2 . . ? H11A C11 H11D 108.4 . . ? H11B C11 H11D 1 . . ? H11C C11 H11D 107.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 Au1 C9 N1 -18(19) . . . . ? Au1 C9 N1 C10 -4E1(2) . . . . ? C1 C7 C8 Au1 3E1(8) . . . . ? C9 Au1 C8 C7 -64(18) . . . . ? C15 C16 C17 C18 -177.8(9) . . . . ? C19 C18 C17 C16 -176.7(9) . . . . ? C8 C7 C1 C6 2E1(7) . . . . ? C8 C7 C1 C2 -16E1(7) . . . . ? C4 O1 C15 C16 -179.3(8) . . . . ? C17 C16 C15 O1 -176.9(9) . . . . ? C4 C5 C6 C1 -1.5(16) . . . . ? C2 C1 C6 C5 0.7(15) . . . . ? C7 C1 C6 C5 -176.9(10) . . . . ? C4 C3 C2 C1 -3.2(15) . . . . ? C6 C1 C2 C3 1.6(14) . . . . ? C7 C1 C2 C3 179.2(9) . . . . ? C9 N1 C10 C11 -26(13) . . . . ? C15 O1 C4 C3 -0.8(14) . . . . ? C15 O1 C4 C5 177.6(9) . . . . ? C2 C3 C4 O1 -179.4(9) . . . . ? C2 C3 C4 C5 2.3(15) . . . . ? C6 C5 C4 O1 -178.5(9) . . . . ? C6 C5 C4 C3 0.0(16) . . . . ? C19 C20 C21 C22 -173(4) . . . . ? C19 C20A C21A C22A 177.8(16) . . . . ? C17 C18 C19 C20 -178(3) . . . . ? C17 C18 C19 C20A 178.8(13) . . . . ? C21 C20 C19 C18 -162(4) . . . . ? C21 C20 C19 C20A -150(18) . . . . ? C21A C20A C19 C18 179.2(16) . . . . ? C21A C20A C19 C20 10(13) . . . . ? C11 C12 C13 C14 72(3) . . . . ? C11 C12A C13A C14A -167.5(19) . . . . ? N1 C10 C11 C12A -177.9(16) . . . . ? N1 C10 C11 C12 172.5(17) . . . . ? C13A C12A C11 C10 -170.1(18) . . . . ? C13A C12A C11 C12 -102(12) . . . . ? C13 C12 C11 C10 135.2(18) . . . . ? C13 C12 C11 C12A 20(9) . . . . ? #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 927047'